Hydrochloric Acid → (Z)-17beta-hydroxy-2-hydroxymethylene-17alpha-methylandrosta-4,15-dien-3-one

HRID 274313ノート

反応式

HRID 274313 の反応式
[CH:1](OCC)=[O:2].[OH:6][C@@:7]1([CH3:27])[CH:12]=[CH:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3.[H-].[Na+].Cl>O1CCCC1.C1(C)C=CC=CC=1>[OH:6][C@@:7]1([CH3:27])[CH:12]=[CH:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])/[C:19](=[CH:1]\[OH:2])/[CH2:20]1)[CH2:15][CH2:14]3

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 1567913617beta-Hydroxy-17alpha-methylandrosta-4,15-dien-3-one

生成物 1

HCID 15679154(Z)-17beta-hydroxy-2-hydroxymethylene-17alpha-methylandrosta-4,15-dien-3-one

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

At room temperature, 4.6 ml of ethyl formate is added to 4.6 g of 17β-hydroxy-17α-methylandrosta-4,15-dien-3-one in 40 ml of tetrahydrofuran and 70 ml of toluene. Then 3.5 g of sodium hydride (60% paraffin suspension) is added in small portions. After 6 hours, the reaction mixture is gently stirred into ice/water which contains hydrochloric acid, the precipitated product is suctioned off, washed with water, dissolved in methylene chloride, dried, and concentrated under vacuum. After chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient, 2.4 g of (Z)-17β-hydroxy-2-hydroxymethylene-17α-methylandrosta-4,15-dien-3-one is obtained, mp 176° C. (from acetone/hexane).

後処理

  1. washwashed with water
  2. dissolutiondissolved in methylene chloride
  3. customdried
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1ca2a8c3dd7d4c99b78dc7b6d360a2b1
出典データセット
uspto-grants-1995_02
特許番号
US05389624

反応ノート

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