Hydrocinnamoyl chloride

This method is general for chloromethyl ketones. Yields of 75-85% may be obtained using hydrocinnamoyl chloride or diphenylacetyl chloride. 

Pyrrolizin-3-ones 75 were synthesized in one step from 2-formylpyrrole derivatives 228 and hydrocinnamoyl chloride in the presence of 4-dimethylaminopyridine (DMAP) and T,iV-diisopropylethylamine (DIPEA), in low to moderate yields (Scheme 57) <2002TL3673>. 

Phenylacetyl chloride and hydrocin-namoyl chloride are reduced at mercury to form both acyl radicals and acyl anions as intermediates [76]. From electrolyses of phenylacetyl chloride, the products include 1,4-diphenyl-2-butene-2,3-diol diphenylac-etate, phenylacetaldehyde, toluene, 1,3-diphenylacetone, and l,4-diphenyl-2,3-butanediol, and analogous species arise from the reduction of hydrocinnamoyl chloride. Reduction of phthaloyl dichloride is a more complicated system [77] the electrolysis products are phthalide, biph-thalyl, and 3-chlorophthalide, but the latter compound undergoes further reduction to give phthalide, biphthalyl, and dihydrobi-phthalide. 

A. 1-Diazo-4-phenyl-2-butanone. A 1-L Erlenmeyer flask equipped with a two-inch magnetic stirring bar and a two-hole rubber stopper fitted with a 125-mL Teflon stopcock separatory funnel (Note 2 and a drying tube filled with potassium hydroxide (Note 3) is charged with a solution of 200 mmol (3.4 equiv) of diazomethane (Note 4) in 600 mL of dry ether. The solution is cooled to 0°C and stirred at high speed (Note 5). To this cooled solution, 10.0 g (59 mmol) of hydrocinnamoyl chloride (3-phenylpropionyl chloride) (Note 6) diluted to 125 mL with anhydrous ether is added dropwise over a 1 -hr period. The resulting reaction mixture is stirred cold for an additional 0.5 hr and then at room temperature for 1 hr. After this period of time the... 

This transient intermediate decarboxylates under reaction conditions to afford the bis(enone) 154. Hydrogenation over platinum proceeds to give the saturated ketone (155). Treatment of 155 with benzylamine in the presence of cyanoborohydride leads to the product from reductive amination (156). Acylation with hydrocinnamoyl chloride affords the amide 157. ... 

Acyl radicals and acyl anions are proposed intermediates in the reduction of phenylacetyl chloride and hydrocinnamoyl chloride at mercury in MeCN [223]. Among the products obtained from the reduction of phenylacetyl chloride are 1,4-diphenyl-2-butene-2,3-diol diphenylacetate, phenylacetaldehyde, toluene, 1,3-diphenyl-acetone, and l,4-diphenyl-2,3-butanediol, as well as phenylacetic acid and phenylacetic acid anhydride. Analogous products arise from the reduction of hydrocinnamoyl chloride l,6-diphenyl-3-hexene-3,4-diol dihydrocinnamate, hydrocinnamaldehyde, ethyl benzene, l,6-diphenyl-3,4-hexanediol, hydrocinnamic acid, and hydrocinnamic acid anhydride. 

A further aldol condensation employing 56 has been reported [13, 28], The chiral linker 56 was N-acetylated with hydrocinnamoyl chloride and finally treated with isovaleraldehyde. The afforded [3-hydroxylated immobilized product was detached... 

The reaction between acid chlorides and a urea nitrogen has also been demonstrated. Hydrocinnamoyl chloride and an imi-dazolidinone were reacted in the presence of DMAP, leading to the formation of an imidazolidinone analog, which has attracted attention for its applicability as an HIV protease inhibitor and a... 

The mixture of 300 mg of alkoxyamine resin, 126 /xL of diisopropylethylamine (0.72 mmol, 10 equiv.), and 53.4 fiL of hydrocinnamoyl chloride (0.36 mmol, 5.0 equiv.) was shaken for 18 hours at room temperature under nitrogen. The resin was filtered and washed sequentially with MeOH (3x5 mL) and dichloromethane (2x5 mL). The resin was then treated with a solution of 2.5% TFA and 1% H2O in 4 mL of dichloromethane, and the mixture was shaken for 1 hour. Resin was filtered and washed sequentially with MeOH (3x5 mL) and dichloromethane (2x5 mL), and then retreated with a solution of 50% TFA and 1% H2O in 4 mL of dichloromethane under shaking for 1 hour. The resin was filtered, and the filtrate was concentrated in vacuo to give crude product which was purified by preparative TLC (5% MeOH in dichloromethane) to give 6.75 mg of hydroxamic acid, in yield of 88%. 

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