Benzyl mercaptan → 21-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1077009ノート

反応式

HRID 1077009 の反応式
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Br[CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1>CC(O)C.C1(C)C=CC=CC=1>[CH2:7]([S:8][CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 7509Benzyl mercaptanHCID 5360545SodiumHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

生成物 1

HCID 8673346821-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

実験手順

Toluene-α-thiol (1.0 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of propan-2-ol (25 ml.) and toluene (30 ml.). 21-Bromo-3α-hydroxy-5α-pregnane-11,20 -dione (0.7 g.) was then added and the mixture was gently refluxed for 2 hr. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was purified by preparative t.l.c. (CHCl3) to give title compound (0.4 g.) as a white foam, [α]D + 89° (c 1.1).

後処理

  1. temperaturethe mixture was gently refluxed for 2 hr
  2. customThe mixture was then partitioned between water and ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by preparative t.l.c

出典と根拠

ORDレコード
ord-be45fe49846a4b849ed0a10e61235ffb
出典データセット
uspto-grants-1976_05
特許番号
US03959260

反応ノート

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