Sodium Bicarbonate → 11beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701458ノート

反応式

HRID 1701458 の反応式
C(=O)(O)[O-].[Na+].ClCC([O:10][C@@H:11]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:27]2[C@@H:26]([O:32][C:33](=[O:36])[CH2:34][Cl:35])[CH2:25][C@@:24]2([CH3:37])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12]1)=O>CO>[Cl:35][CH2:34][C:33]([O:32][C@H:26]1[CH2:25][C@@:24]2([CH3:37])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:27]1[C@:28]1([CH3:31])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:10])[CH2:30][CH2:29]1)=[O:36]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 867368843alpha,11beta-Bischloroacetoxy-5alpha-pregnan-20-one

生成物 1

HCID 8673686911beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one収率 78.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Saturated sodium bicarbonate solution (200 ml) was added slowly to a stirred refluxing solution of 3α,11β-bischloroacetoxy-5α-pregnan-20-one (89 g) in methanol (1800 ml). After about 3.5 hours the mixture was evaporated to half its volume, water was added and the steroid was extracted with ethyl acetate. The washed and dried extract was evaporated in vacuo, the residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1) and crystallised from ethyl acetate-petroleum ether to afford title compound (59 g), m.p. 83°-86°, [α]D +101° (c 1.0).

後処理

  1. customAfter about 3.5 hours the mixture was evaporated to half its volume, water
  2. additionwas added
  3. extractionthe steroid was extracted with ethyl acetate
  4. washThe washed
  5. customdried
  6. extractionextract
  7. customwas evaporated in vacuo
  8. filtrationthe residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1)
  9. customcrystallised from ethyl acetate-petroleum ether

出典と根拠

ORDレコード
ord-a689ca136b554e0e8cbda14410413f79
出典データセット
uspto-grants-1980_03
特許番号
US04192871

反応ノート

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