Reaktion #71598

Reaktionsgleichung

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

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared by a method analogous to
2. 2
   workup.ADDITIONOnce the addition
3. 3
   Sonstigeis removed
4. 4
   workup.ADDITIONThe reaction mixture is diluted with dichloromethane (35 ml)
5. 5
   Waschenwashed with saturated aqueous sodium bicarbonate solution (20 ml)
6. 6
   TrocknenThe organic phase is dried over anhydrous magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe filtrate is evaporated in vacuo
9. 9
   SonstigeThe residue is purified by column chromatography on silica gel
10. 10
    Wascheneluting with a mixture of ethyl acetate and hexane

Vorschrift

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.

Quelle