Potassium triethylamine

Alternatively, use the following procedure in which triethylamine replaces potassium acetate as the basic catalyst. Place 2 1 g. (2-0 ml.) of purified benzaldehyde, 2 0 ml. of anhydrous triethylamine and 5 0 ml. of A.R. acetic anhydride in a 200 ml. round-bottomed flask, equipped with a short reflux condenser and a calcium chloride drying tube. Boil the solution gently for 24 hours—heating may be interrupted. Incorporate a steam distillation apparatus in the flask and steam distil until the distillate is no longer cloudy (about 100 ml.) and then collect a further 50 ml. of the distillate di ard the steam distillate. Transfer the residue in the flask to a 400 ml. beaker, add water until the vplume is about 200 ml., then 0 2 g. of decolourising carbon, and boil for a few minutes. Filter the hot solution, and acidify the hot filtrate with 1 1 hydrochlorioiaoid... 

This experiment describes the quantitative analysis of the asthma medication Quadrinal for the active ingredients theophylline, salicylic acid, phenobarbital, ephedrine HGl, and potassium iodide. Separations are carried out using a Gi8 column with a mobile phase of 19% v/v acetonitrile, 80% v/v water, and 1% acetic acid. A small amount of triethylamine (0.03% v/v) is included to ensure the elution of ephedrine HGl. A UV detector set to 254 nm is used to record the chromatogram. 

A 600-mL, three-necked, round-bottomed flask 1s equipped with a mechanical stirrer, a short gas inlet tube, and an efficient reflux condenser fitted with a potassium hydroxide drying tube. The flask is charged with 13.4 g (0.05 mol) of 3-ben2y1-5-(2-hydroxyethyl)-4-methyl-l,3-th1azol1um chloride (Note 11, 72.1 g (1.0 mol) of butyraldehyde (Note 2). 30.3 g (0.3 mol) of triethylamine (Note 2), and 300 raL of absolute ethanol. A slow stream of nitrogen (Note 3) is begun, and the mixture is stirred and heated In an oil bath at 80°C. After 1.5 hr the reaction mixture is cooled to room temperature and concentrated by rotary evaporation. The residual yellow liquid Is poured Into 500 mL of water contained 1n a separatory funnel, and the flask is rinsed with 150 mL of dichloromethane which is then used to extract the aqueous mixture. The aqueous layer is extracted with a second 150-mL portion of... 

In contrast to phosphorus esters, sulfur esters are usually cleaved at the carbon-oxygen bond with carbon-fluorine bond formation Cleavage of esteri nf methanesulfonic acid, p-toluenesidfonic acid, and especially trifluoromethane-sulfonic acid (tnflic acid) by fluoride ion is the most widely used method for the conversion of hydroxy compounds to fluoro derivatives Potassium fluoride, triethylamine trihydrofluoride, and tetrabutylammonium fluoride are common sources of the fluoride ion For the cleavage of a variety of alkyl mesylates and tosylates with potassium fluoride, polyethylene glycol 400 is a solvent of choice, the yields are limited by solvolysis of the leaving group by the solvent, but this phenomenon is controlled by bulky substituents, either in the sulfonic acid part or in the alcohol part of the ester [42] (equation 29)... 

Although bromo derivatives have been used, the two most common ot-halocarbonyl compounds for this reaction are chloroacetaldehyde and chloroacetone. The dicarbonyl component is typically ethyl acetoacetate or one of its derivatives. A variety of bases including triethylamine and potassium hydroxide can promote the reaction however, the most popular base is pyridine. Conversion to the furan takes place either at room temperature or upon heating to 50°C with reaction times varying from four hours to five days and yields ranging from 30-86%. 

To a solution of 112 (2.0 g, 43.0 mmol) in 50 mL of dry THF at -65°C was added a solution of 111 (4.45 g, 34.0 mmol) in 100 mL of absolute ethanol containing 5 mL of acetic acid cooled to - 65°C in one portion. After stirring for 15 min., dry triethylamine (4.8 g, 510 mmol) was added. The reaction continued for 24 h with slow warming to room temperature before reducing the volume to 10 mL. The crude 113 was brought to pH 10 with potassium carbonate. The aqueous solution was continuously extracted with chloroform, dried (K2CO3), evaporated onto neutral alumina, placed on a column of neutral alumina (50 g) and eluted with chloroform. The solvent was evaporated and the residue crystallized from ethanol to yield 113 (2.86 g 55%). The yellow solid had a mp = 72.5-73.8°C. 

The hydroxy compound 59 has been acetylated (94AJC991), and many glycosides have been protected by acetylation. The 4-thione 209 (85LA1922) and the 3-thiol 210 (83USP4419516) have been alkylated using methyl iodide with potassium hydroxide and chloroacetonitrile with triethylamine respectively. 

Treatment of 460 with triethylamine in DMSO gave 15% of 461. This compound was also obtained from spiro complex 462 formed from 460 by the action of potassium rerr-butoxide (Scheme 73) (74ZOR826, 78ZOR105). 

Preparation of 2-Cyclopropylcarbony/amido-5-Chlorobenzophenone To 400.5 g (1.73 mols) of 2-amino-5-chlorobenzophenone dissolved in 220 g (2.18 mols) of triethylamine and 3.5 liters of tetrahydrofuran is added cautiously 181 g (1.73 mols) of cyclopropane-carboxylic acid chloride. The reaction is refluxed 2 /2 hours and allowed to cool to room temperature. The solvent is then removed under vacuum to obtain 2-cyclopropylcarbonyl-amido-5-chlorobenzophenone as a residue which is dissolved in 1 liter of methylene chloride, washed twice with 5% hydrochloric acid, and then twice with 10% potassium hydroxide. The methylene chloride solution is then dried over anhydrous magnesium sulfate, filtered and the solvent removed under vacuum. The residue is recrystallized from 1,500 ml of methanol, charcoal-treating the hot solution to give 356 g of 2-cyclopropylcarbonylamido-5-chlorobenzophenone, MP 105° to 105.5°C (69% yield). 

Triethylamine is freshly distilled and stored over potassium hydroxide pellets. 

Oxabicyclo[4.1.0]hept-3-enes with a bromo substituent in position 2 can be converted to oxepins 11 by reaction with an appropriate base such as potassium ter+butoxide or triethylamine (see the experimental procedures for the preparation of the parent system in Houben-Weyl, Vol. 6/ld, pi78 and Vol. 6/4, p462).12,156,157 Usually the reaction products are mixtures of oxepin 11 and benzene oxide 12. In the case of ZerZ-butyl 7-oxabicyclo[4,1.0]hept-3-ene-2-carboxylate, the equilibrium lies completely on the benzene oxide side 12a.158... 

A solution of the primary amine (lOmmol), t-butylchlorodiphenylsilane (lOmmol), and triethylamine (15mmol) in MeCN (30ml) was stirred at ambient temperature for 1-3 h. The reaction mixture was concentrated in vacuo, and the residue was partitioned between hexane/AcOEt (4 1), and 1 M sodium hydrogen carbonate solution. The organic phase was dried over a mixture of potassium carbonate and sodium sulphate. 

The submitters used Baker-grade triethylamine purchased from J. T. Baker Chemicals N.V., P.O. Box 1, Deventer, Holland, after distillation from potassium hydroxide. 

Finally, in the case of 30 made by Holmes and coworkers, the starting material was tris(o-tolyl)phosphine, which was treated sequentially with potassium permanganate and HCl to generate phosphorane 36, which was then treated with triethylamine to yield the desired phosphate 30 in 64% yield as its Et3NH salt [49,50] (Scheme 6). 

To mention a few synthetic appHcations of trialkylsilanols, trimethylsilanol 4 adds readily to 2-chloroacrylonitrile in diethyl ether in the presence of triethylamine as triethylammonium trimethylsilanolate followed by ehmination of triethylamine hydrochloride to give 99 [32] (cf. discussion of the strongly nucleophihc properties of ammonium trimethylsilanolate 155 in Section 4.2.1). The stable potassium trimethylsilanolate 97 has also been used for the saponification of esters (Section 4.7). Dimethylphenylsilanol 100 adds readily to a,y9-unsaturated carbonyl compounds such as methyl vinyl ketone 764 in the presence of Pd(OAc)2 in a Heck-Suzuki-type reaction to give the sihcon-free /9-phenylmethylvinylketone 101 [33]. 

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