Propionyl iodide

Subsequent insertion of CO into the newly formed alkyl-ruthenium moiety, C, to form Ru-acyl, D, is in agreement with our 13C tracer studies (e.g., Table III, eq. 3), while reductive elimination of propionyl iodide from D, accompanied by immediate hydrolysis of the acyl iodide (3,14) to propionic acid product, would complete the catalytic cycle and regenerate the original ruthenium carbonyl complex. 

Polyethylene glycol (molecular weight, 300-6(W) can aid in the displacement of activated halogen by fluorine. Propionyl chloride is converted to propionyl fluoride with potassium fluoride and polyethylene glycol in acetonitrile [63] Treatment of benzyl chloride with a mixture of potassium fluoride and potassium iodide for 5 h in acetonitrile containing polyethylene glycol 200 gives benzyl fluoride in 62% yield [64],... 

Bruce and Sutcliffe obtained l-acetyl-2-methyl-3-phenylindole (123) by the action of acetyl chloride on 2-methyl-3-pheiiylindole magnesium iodide in ether.These authors were able to obtain l-benzoyl-2-benzyl-3-phenylindole (124) but not l-acetyl-2-benzyl-3-phenylindole (125) from 2-benzyl-3-phenylindole magnesium iodide by analogous procedures.3-Acetyl-2-phenylindole (126) and 3-propionyl-2-pheny]indole (127) have recently been prepared in fair yield by the acylation of 2-phenylindole magnesium iodide with acetyl and propionyl chloride, respectively. Le ete obtained a mixture of l-acetyl-3-ethylindole (128) and 2-acetyl-3-ethylindole (129) by the interaction of acetyl chloride with 3-ethylindole magnesium iodide in ether. 

In an attempt to prepare ethyl 3-indolylacetate (225) by the action of ethyl chloroacetate on indole magnesium iodide, only unidentified oily products were obtained under a variety of different experimental conditions. However, when indole magnesium iodide was treated with ethyl -chloropropionate in other, a product, identified as 3-[)3-(l-indolyl)propionyl]indole (226) by its behavior on alkaline hydrolysis and by the number of active hydrogen atoms it contained, was obtained. ... 

The retrosynthetic analysis of the target molecule 47, which is shown in Scheme 9.16, allows to reduce it to very simple starting materials, such as 2-methyl-2-propene iodide (55) and the chiral A -propionyl-2-oxazolidone 48. The... 

An ester of alanine with an arylaliphatic alcohol has shown promise as a non-tricyclic aiitidepressaiit. It may be speeulated that the hindered milieu of the ester linkage protects the compound from hydrolysis by endogenous esterases. The preparation starts by reaction of pheny-lacctate 83 with methyl magnesium iodide to give tertiary carbinol 84. Acylation with 2-bromo-propionyl bromide leads to ester 85 displacement of halogen with ammonia leads to alaproclate ( 6) [211. 

Similarly the enantiomerically pure bicyclic A -propionyl lactam 9 can be enolized and reacted with allyl iodide to give a 56% yield of the alkylation product 10 (d.r. 98 2), which when hydrolysed furnishes (7 )-2-methyl-4-pentenoic acid (11)5. 

Table 1. Addition of Methylmagnesium Iodide to syn and anti 2-Propionyl-2-methyl-1,3-dithiane 1-Oxide Substrates...

The ethyl derivative, however, was not isolated in a pure form it was always contaminated by traces of solvent. Then, in 1963, Davison et al. (14) reported the synthesis of the ethyl and propionyl derivatives. The ethyl compound was isolated in a pure form from the treatment of Na[Re(CO)s] with ethyl iodide. [Re(C2H5)(CO)s] was also found to be much less susceptible to carbonylation than [Mn(C2H5)(CO)5] and was therefore considerably more stable the reaction between [Re(C2H5)(CO)5] and CO (100 atm) to form [Re(COC2H5)(CO)5] was still not complete after 1 hour at 100°C (14). 

After some optimization, it was found that propionyl and acetyl derivatives of anilines can be efficiently arylated under conditions similar to the ones described above (Scheme 9) [50], Electron-rich as well as electron-poor anilides are reactive. Aryl iodides of all electronic properties can be used however, o/f/io-substitution is not tolerated. Propionylanilides are arylated in somewhat higher yields than acetanilides. 

Preparative Methods from propionyl chloride and 1,3-thiazo-lidine-2-thione in the presence of triethylamine, or from propionic acid and thiazolidine-2-thione in the presence of triethylamine and 2-chloro- 1-methylpyridinium iodide. Handling, Storage, and Precautions use in a fume hood. 

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