Reacción #71598

Ecuación de reacción

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

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared by a method analogous to
2. 2
   workup.ADDITIONOnce the addition
3. 3
   Otrois removed
4. 4
   workup.ADDITIONThe reaction mixture is diluted with dichloromethane (35 ml)
5. 5
   Lavadowashed with saturated aqueous sodium bicarbonate solution (20 ml)
6. 6
   SecadoThe organic phase is dried over anhydrous magnesium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe filtrate is evaporated in vacuo
9. 9
   OtroThe residue is purified by column chromatography on silica gel
10. 10
    Lavadoeluting with a mixture of ethyl acetate and hexane

Procedimiento

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.

Fuente