反応 #71598

反応方程式

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

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他prepared by a method analogous to
2. 2
   workup.ADDITIONOnce the addition
3. 3
   その他is removed
4. 4
   workup.ADDITIONThe reaction mixture is diluted with dichloromethane (35 ml)
5. 5
   洗浄washed with saturated aqueous sodium bicarbonate solution (20 ml)
6. 6
   乾燥The organic phase is dried over anhydrous magnesium sulphate
7. 7
   ろ過filtered
8. 8
   その他the filtrate is evaporated in vacuo
9. 9
   その他The residue is purified by column chromatography on silica gel
10. 10
    洗浄eluting with a mixture of ethyl acetate and hexane

実験手順

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.

出典