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

HRID 274313노트

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HRID 274313 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1ca2a8c3dd7d4c99b78dc7b6d360a2b1
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389624

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