반응 #71598

반응 방정식

triethylamine

2-(2,4,6-trimethylphenyl)-5-(tetrahydrofuran-3-yl)cyclohexane-1,3-dione

acetyl chloride

→

3-oxo-5-(tetrahydrofuran-3-yl)-2-(2,4,6-trimethylphenyl)cyclohex-1-enyl acetate

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타prepared by a method analogous to
2. 2
   workup.ADDITIONOnce the addition
3. 3
   기타is removed
4. 4
   workup.ADDITIONThe reaction mixture is diluted with dichloromethane (35 ml)
5. 5
   세척washed with saturated aqueous sodium bicarbonate solution (20 ml)
6. 6
   건조The organic phase is dried over anhydrous magnesium sulphate
7. 7
   여과filtered
8. 8
   기타the filtrate is evaporated in vacuo
9. 9
   기타The residue is purified by column chromatography on silica gel
10. 10
    세척eluting with a mixture of ethyl acetate and hexane

실험 절차

A solution of triethylamine (0.11 ml, 0.79 mmol) in dichloromethane (2 ml) is added dropwise to a chilled (ice-bath) solution of 2-(2,4,6-trimethylphenyl)-5-(tetrahydrofuran-3-yl)cyclohexane-1,3-dione (prepared by a method analogous to that described in Example 2) and acetyl chloride (0.056 ml, 0.79 mmol) in dichloromethane (4.5 ml). Once the addition is complete the cooling bath is removed and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with dichloromethane (35 ml) and washed with saturated aqueous sodium bicarbonate solution (20 ml). The organic phase is dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 3-oxo-5-(tetrahydrofuran-3-yl)-2-(2,4,6-trimethylphenyl)cyclohex-1-enyl acetate.

출처