Benzoyl chloride → 15alpha-Benzoyloxyestra-4,9-diene-3,17-dione
Reaction equation
[OH:1][C@@H:2]1[C@H:7]2[C@H:8]3[C:17]([CH2:18][CH2:19][C@:5]2([CH3:6])[C:4](=[O:21])[CH2:3]1)=[C:16]1[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:22]([O:1][C@@H:2]1[C@H:7]2[C@H:8]3[C:17]([CH2:18][CH2:19][C@:5]2([CH3:6])[C:4](=[O:21])[CH2:3]1)=[C:16]1[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 20 g of 15α-hydroxyestra-4,9-diene-3,17-dione in 120 ml of pyridine is combined dropwise with 13.6 ml of benzoyl chloride and the mixture is stirred for one hour at room temperature. Subsequently the mixture is poured into ice water, extracted with dichloromethane, washed with sodium bicarbonate solution and water and concentrated under vacuum. The cooled crude product is chromatographed on silica gel, yielding 26.2 g of 15α-benzoyloxyestra-4,9-diene-3,17-dione.