반응 #335236

반응 방정식

4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester

sodium cyanide

→

title compound

수율 11.4%

4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

수율 11.4%

용매

ammonium chloride

hexamethylphosphoramide

반응 조건

후처리

1. 1
   온도cool
2. 2
   추출Extract with ethyl ether (400 mL)
3. 3
   세척wash with water (2×300 mL)
4. 4
   건조brine (300 mL) and dry (MgSO4)
5. 5
   기타Evaporate the solvent in vacuo
6. 6
   기타purify by flash chromatography (5→10% methanol/chloroform)

실험 절차

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester (10 g, 32.4 mmol) in anhydrous hexamethylphosphoramide (160 mL) and treat with sodium cyanide (1.59 g, 32.4 mmol). Heat at 70° C. for 48 hours, cool and dilute with saturated ammonium chloride (300 mL). Extract with ethyl ether (400 mL), wash with water (2×300 mL), then brine (300 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (5→10% methanol/chloroform) to give the title compound (1.09 g).

출처