Acetic Acid → 13-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17beta-ol

HRID 1077222Notes

Reaction equation

HRID 1077222 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH2:18][CH3:19])[C@H:16]([C@@H:8]3[CH2:7][CH:6]([CH3:23])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]4=[O:17].[BH4-].[Na+].C(O)(=O)C>CO.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH2:18][CH3:19])[C@H:16]([C@@H:8]3[CH2:7][CH:6]([CH3:23])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C@@H:13]4[OH:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 6814340513-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-one

Product 1

HCID 6814444413-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17beta-olYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Dissolve dl-3-methoxy-6-methyl-13-ethylgona-1,3,5(10)-trien-17-one (7.0 g) in methanol (300 cc) and treat with sodium borohydride (3.0 g). After spontaneous reflux ceases, make acid with 50% aqueous acetic acid (20 cc). Pour into brine, extract with acid and isolate the dl-3-methoxy-17β-hydroxy-6-methyl-13-ethylgona-1,3,5(10)-triene (6.8 g), m.p. 150°-160°C, λ max. KBr 3.05, 6.45 μ.

Workup

  1. temperatureAfter spontaneous reflux ceases
  2. extractionextract with acid

Sources & evidence

ORD record
ord-cae042231bef41c08be320c29371458a
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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