Hydrochloric Acid → HCID 86733309、化合物

HRID 1606377ノート

反応式

HRID 1606377 の反応式
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH:10]=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:1][C@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[CH2:17][CH2:16][C@@:15]3([CH3:23])[C@H:8]4[CH2:9][CH:10]=[C:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 1775252(3β,5α)-3-Hydroxypregn-16-en-20-one

生成物 1

HCID 86733309HCID 86733309、化合物収率 89.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3β-Hydroxy-5α-pregn-16-en-20-one (10 g.) in pyridine (50 ml.) was treated with toluene-p-sulphonyl chloride (10 g.), and the solution was stirred at room temperature overnight and then poured into dilute hydrochloric acid. The precipitate was extracted into chloroform, and the extract was washed with dilute hydrochloric acid and with water, dried over sodium sulphate and evaporated to an oil which crystallised on standing. Recrystallisation from ethyl acetate/petrol gave 3β-toluene-p-sulphonyloxy-5α-pregn-16-en-20-one (13.3g) as off-white prisms, m.p. 146°-148° , [α]D + 24.0°, λmax. (EtOH) 226.5 nm (ε 18,600), 240 nm (infl.) (ε 9550), 272.5 nm (ε 518).

後処理

  1. extractionThe precipitate was extracted into chloroform
  2. washthe extract was washed with dilute hydrochloric acid and with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to an oil which
  5. customcrystallised
  6. customRecrystallisation from ethyl acetate/petrol

出典と根拠

ORDレコード
ord-f6c26d8628ad4f6eb18ed8a7cce8189e
出典データセット
uspto-grants-1976_04
特許番号
US03952031

反応ノート

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