反応 #65024

反応方程式

ethyl acetate

potassium carbonate

title acid

α-methylenebenzenepropanoic acid

benzyl bromide

→

title compound

収率 60.1%

phenylmethyl α-methylenebenzenepropanoate

収率 60.1%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate
3. 3
   洗浄washed with 3 times of water, brine
4. 4
   乾燥The solution was dried (Na2SO4)
5. 5
   その他evaporated
6. 6
   その他The residue was purified by flash chromatography on silica gel
7. 7
   洗浄eluting with 90:10 heptane

実験手順

The title acid of Step 9 (5.2 g, 30 mmol) was dissolved in dimethylformamide (25 mL) and cooled to 0° C. To this potassium carbonate (5.7 g, 41.48 mmol) was added followed by benzyl bromide (5.7 g, 29.7 mmol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with 3 times of water, brine. The solution was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting with 90:10 heptane:ethyl acetate to give the pure title compound as colorless oil (4.5 g, 60% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C17H16O2 : C, 80.93; H, 6.39. Found: C, 80.69; H, 6.47.

出典