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

HRID 1414999Notes

Reaction equation

HRID 1414999 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-490db63b19624d82b4f52c3cf8a614a0
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

Loading…