Ethanol → 2beta-Ethoxy-3alpha-hydroxy-5alpha-androstan-11-one-17beta-carboxylic acid

反応式

[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][C:16]1=[O:21])([CH3:14])[C@@H:12]([C:22]([OH:24])=[O:23])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)O.O.[CH2:31]([OH:33])[CH3:32]>>[CH2:31]([O:33][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C:16](=[O:21])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:22]([OH:24])=[O:23])[CH2:4][C@@H:3]1[OH:1])[CH3:32]

参加物

反応物 4

HCID 702Ethanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 22788254HCID 22788254、化合物

生成物 1

HCID 227882552beta-Ethoxy-3alpha-hydroxy-5alpha-androstan-11-one-17beta-carboxylic acid

実験手順

A solution of 2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid (940 mg.) and concentrated sulphuric acid (0.25 ml.) in dry ethanol (30 ml.) was stirred at room temperature for 30 minutes. Water (100 ml.) was added and the reaction mixture extracted with chloroform. The chloroform solution was washed with water, dried, filtered and evaporated to give a froth which solidified when triturated with chloroform/petrol. Filtration afforded the solid crude product (752 mg.) which, after recrystallisation from ethanol/water, afforded the pure title compound; m.p. 249°-260°; [α]D + 74°, (c 0.33).