反応 #2383787

反応方程式

Sodium

ethyl mercaptoacetate

allyl 4-chlorobutyrate

→

title compound

収率 88.1%

Allyl 4-(ethoxycarbonylmethylthio)butyrate

収率 88.1%

溶媒

allyl alcohol

反応条件

後処理

1. 1
   workup.ADDITIONThe obtained solution was treated
2. 2
   温度for 1 hour at reflux temperature
3. 3
   濃縮The mixture was concentrated by evaporation
4. 4
   workup.ADDITIONpoured into a mixture of diethylether (200 ml) and of an ice/water mixture (100 g)
5. 5
   その他The ether phase was separated
6. 6
   抽出the obtained aqueous phase was extracted with diethyl ether (200 ml)
7. 7
   洗浄The combined ether fractions were washed with water (200 ml) and 4% aqueous sodium hydrogencarbonate solution (200 ml)
8. 8
   乾燥dried with magnesium sulfate
9. 9
   その他After the removal of the drying agent and evaporation of ether

実験手順

Sodium (9.06 g; 0.39 mole) was decomposed in allyl alcohol (380 ml). The obtained solution was treated by dropwise adding of first ethyl mercaptoacetate (42.7 ml; 0.39 mole) at the temperature of 0° C. and then of allyl 4-chlorobutyrate (58.3 g; 0.36 mole) prepared according to the process disclosed in Example 2a. The obtained mixture was stirred for three hours at room temperature and then for 1 hour at reflux temperature. The mixture was concentrated by evaporation and poured into a mixture of diethylether (200 ml) and of an ice/water mixture (100 g). The obtained solution was acidified with 1M hydrochloric acid solution to achieve a pH value of the medium between 3 and 6. The ether phase was separated and the obtained aqueous phase was extracted with diethyl ether (200 ml). The combined ether fractions were washed with water (200 ml) and 4% aqueous sodium hydrogencarbonate solution (200 ml) and dried with magnesium sulfate. After the removal of the drying agent and evaporation of ether, the title compound (78.1 g; 84%) was obtained, which was used in the crude form in the next reaction.

出典