반응 #1738985

반응 방정식

ammonium chloride

3,4 -methylenedioxybenzaldehyde

methyl propiolate

n-butyllithium

→

methyl 4-hydroxy-4-[3,4-(methylenedioxy) phenyl]-2-butynoate

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at -78° for a further 20 minutes
2. 2
   기타brought to room temperature
3. 3
   추출The aqueous phase was extracted twice with ether
4. 4
   세척The combined organic phases were washed in succession with saturated sodium chloride solution and with water
5. 5
   건조dried over sodium sulphate
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

실험 절차

A solution of 5 ml (60 mmol) of methyl propiolate in 60 ml of tetrahydrofuran was treated at -78° under argon with 37.5 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 9 g 60 mmol) of 3,4 -methylenedioxybenzaldehyde in 60 ml of tetrahydrofuran was added within 30 minutes. The reaction mixture was stirred at -78° for a further 20 minutes, then brought to room temperature and treated with 80 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed in succession with saturated sodium chloride solution and with water, dried over sodium sulphate and concentrated. The residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained methyl 4-hydroxy-4-[3,4-(methylenedioxy) phenyl]-2-butynoate as a brown oil.

출처