Hydrochloric Acid → 5alpha-Pregn-2-en-20-one

HRID 232794

反応式

HRID 232794 の反応式
C1(C)C=CC(S(O[C@@H:11]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:17]4[CH2:18][CH2:19][C@@H:20]3[C:21](=[O:23])[CH3:22])[CH2:12]2)(=O)=O)=CC=1.Cl>N1C(C)=CC(C)=CC=1C>[CH3:22][C:21](=[O:23])[C@@H:20]1[C@:24]2([CH3:32])[C@H:17]([C@H:16]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:31])[C@H:13]([CH2:12][CH:11]=[CH:30][CH2:29]2)[CH2:14][CH2:15]3)[CH2:18][CH2:19]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 538852373alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

生成物 1

HCID 2468835alpha-Pregn-2-en-20-one収率 97%

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

The crude product 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one in 30 mL of collidine was refluxed for 1.0 h. The solution was allowed to cool and then poured into cold dilute hydrochloric acid (200 mL) and extracted three times with CH2Cl2 (100 mL portions). The combined organic phase was dried over magnesium sulfate and concentrated. Flash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20) gave 4.65 g (97% yield for the two steps) of 5α-pregn-2-ene-20-one.

後処理

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2 (100 mL portions)
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washFlash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20)

出典と根拠

ORDレコード
ord-353428eb7881432f849ffb17c593adff
出典データセット
uspto-grants-1997_01
特許番号
US05591733

関連ノート

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