Ferf-Butyl acetate

In the presence of a strong base, the ot carbon of a carboxylic ester can condense with the carbonyl carbon of an aldehyde or ketone to give a P-hydroxy ester, which may or may not be dehydrated to the a,P-unsaturated ester. This reaction is sometimes called the Claisen reaction,an unfortunate usage since that name is more firmly connected to 10-118. In a modem example of how the reaction is used, addition of tert-butyl acetate to LDA in hexane at -78°C gives the lithium salt of ferf-butyl acetate, " (12-21) an enolate anion. Subsequent reaction a ketone provides a simple rapid alternative to the Reformatsky reaction (16-31) as a means of preparing P-hydroxy erf-butyl esters. It is also possible for the a carbon of an aldehyde or ketone to add to the carbonyl carbon of a carboxylic ester, but this is a different reaction (10-119) involving nucleophilic substitution and not addition to a C=0 bond. It can, however, be a side reaction if the aldehyde or ketone has an a hydrogen. 

C5H10O3 Methyl cellosolve acetate ferf-Butyl acetate... 

Acetamidofluorene, see 2-Acetylaminofluorene 2-Acetaminofluorene, see 2-Acetylaminofluorene Acetanhydride, see Acetic anhydride Acetasol, see Acetic acid Acetdimethylamide, see A,A-Dimethylacetamide Acetic acid, amyl ester, see Amyl acetate Acetic acid anhydride, see Acetic anhydride Acetic acid (aqueous soln), see Acetic acid Acetic acid, 2-butoxy ester, see sec-Butyl acetate Acetic acid, butyl ester, see Butyl acetate Acetic acid, sec-butyl ester, see sec-Butyl acetate Acetic acid, ferf-butyl ester, see ferf-Butyl acetate Acetic acid dimethylamide, see A,A-Dimethylacetamide Acetic acid, 1,3-dimethylbutyl ester, see sec-Hexyl acetate Acetic acid, 1,1-dimethylethyl ester, see ferf-Butyl acetate Acetic acid, ethenyl ester, see Vinyl acetate... 

Dimethyl acetate, see ferf-Butyl acetate Dimethylacetone amide, see iV,iV-Dimethylacetamide Dimethylacetonyl carbinol, see Diacetone alcohol Dimethylacetyl formaldehyde, see Methylal Dimethylamide acetate, see iV,iV-Dimethylacetamide iV,iV-Dimethylamine, see Dimethylamine... 

UN 1123, see sec-Bntyl acetate, Bntyl acetate, ferf-Butyl acetate... 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

For the condensation with the properly derivatized lysine part (112) 3 -terf-butyl-1,5-di-Af-hydroxysuccinimidyl citrate (113) was used (Chart 10). It was prepared from 1,5-dimethyl citrate by reaction with ferf-butyl acetate, alkaline hydrolysis of the methyl ester and coupling with W-hydroxysuccinimide by DCCI (257). 

The Michael additions of various carbon nucleophiles such as cyanide [15b, 22b], anions generated from nitromethane [27], ferf-butyl acetate [9], malon-ates [27] and O Donnell s glycine equivalent [541, cuprates [9,15b] or Grignard reagents [53] under copper catalysis [55] have also been reported (Scheme 24). 

There are also some examples of solvates (as opposed to hydrates) that have been reported to exhibit differing bioavailability. For instance, for implants of the methanol solvate of predisolone fert-butyl acetate the mean absorption rate was found to be 4.7 times that of the anhydrous form, which in turn was similar to the hemiacetone solvate (Ballard and Biles 1964). The same authors also reported that the mean absorption rate for all solvates of cortisol ferf-butyl acetate were significantly different from that of the anhydrous form. 

Transesterification with ferf-Butyl Acetate General Procedure ... 

Butyl acetate (BYOO-til AS-uh-tate) exists in three isomeric forms. Isomers are two or more forms of a chemical compound with the same molecular formula, but different structural formulas and different chemical and physical properties. Their names and synonyms are as follows n-butyl acetate is known as butyl ester, or butyl ethanoate -butyl acetate is called i-methylpropyl ester and acetic acid -butyl ester and ferf-butyl acetate is known by 1,1,-dimethylethyl ester or acetic acid, ferf-butyl ester. The expanded chemical formulas for the forms are slightly different n-butyl acetate, CH3C00CH2CH2CH2CH3 -butyl acetate, CH3COOCH(CH3)(C2H5) and ferf-butyl acetate, CH3C00C(CH3)3. 

The actual umpolung reaction that allows a ketene dithioacetal to function as if it had an electrophilic carbon a to a carbonyl is achieved by conjugate addition of nucleophiles to the ketene dithioacetal, followed by hydrolysis. Both sulfide and sulfoxide ketene derivatives can be used. Conjugate addition of an ester enol-ate derived from ferf-butyl acetate (secs. 9.2, 9.4.B, 9.7.A) to the ketene dithioacetal [CH2=C(SOMe)2] gave the stable dithioacetal anion (382). Conversion of the dithioacetal to the bis(sulfoxide) enhanced the ability of that species to function as a Michael acceptor. Subsequent transformation of 382 gave the aldehyde-ester (383).370... 

Oxy-y-butyrolactones are substructural units in many biologically interesting natural products, accessible by nucleophilic addition of the enolates of tert-butyl acetate on epoxy pentuloses. The hthium enolate of ferf-butyl acetate is reacted with the epoxy ketose 50 (generated from 49) in a mixture of THF/HMPA (3 1) to afford 51 and 52. However, the frans-oriented isomer 52 can only be converted to the desired lactone 54 on treatment with TFA in CH2CI2 at room temperature for 30 min [18] (Scheme 11). 

C6H12O2 ferf-Butyl acetate 293.2 5.672 0.55435E+02 -0.30494E+00 0.46107E-03 273-323... 

Please see Figure 13.7 for the spectrum of ferf-butyl acetate (1). 

DL-Phenylalanine, a large excess of ferf-butyl acetate, and a slight excess of aq. 60%-HG104 shaken ca. 15 min., stored 4 days at room temp., and the product isolated as the hydrochloride ferf-butyl DL-phenylalaninate hydrochloride. Y 75%. F. e. s. E. Taschner et al., A. 6A6, 134 (1961). 

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