Water → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

HRID 1077181

반응식

HRID 1077181 반응식
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].O>CO.Cl>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

참가 물질

5

반응물 2

HCID 962WaterHCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

생성물 1

HCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-수율 52.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

Add to 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (1.0 g.) in methanol (50 cc.), 3N hydrochloric acid (20 cc.); shake the mixture for 2 hours, pour into water, and extract the product with ether. Work up in the usual way and take up the resulting gum in benzene and chromatograph on neutral alumina. Elute with ether to give a crystalline material and recrystallize from a mixture of ether and pentane to yield 13β-ethyl-17β-hydroxy-gon-4-en-3-one (0.5 g.), m.p. 144°-7°; ultra-violet absorption peak at 240 mμ (ε15,500); infrared absorption peaks at 2.94, 6.06, 6.23 μ.

후처리

  1. extractionextract the product with ether
  2. washElute with ether
  3. customto give a crystalline material
  4. customrecrystallize from a mixture of ether and pentane

출처 및 근거

ORD 기록
ord-36f78c3e783444699b8e687b5a30cec9
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

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