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

HRID 1077229Notes

Reaction equation

HRID 1077229 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:23])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:23])[CH3:2]

Participants

5

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 1

HCID 887MethanolSolvent

Procedure

Dissolve dl-13-ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-one (7.0 g) in methanol (300 ml) and treat with sodium borohydride (3.0 g). After spontaneous reflux ceases, acidify the reaction mixture with 50% acetic acid (20 ml). Work up by the usual procedures to obtain dl-13-ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17β-ol (6.8 g), m.p. 158°-160°; infrared absorption peaks (potassium bromide) at 3.05 μ, 6.45 μ.

Workup

  1. temperatureAfter spontaneous reflux ceases

Sources & evidence

ORD record
ord-a0552e7bf9e1416b9f6b4bf9104341d6
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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