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

HRID 1415001Notes

Reaction equation

HRID 1415001 reaction equation
[BH4-].[Na+].[CH2:3]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C:6]2=[O:23])=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH3:4].C(O)(=O)C>C(O)C>[CH2:3]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:23])=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 1037926413-Ethylgon-4-ene-3,17-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add sodium borohydride (200 mg.) in ethanol (25 cc.) to 13β-ethylgon-4-en-3,17-dione (1 g.) in ethanol (50 cc.) at 8°. After 15 minutes add an excess of acetic acid and evaporate the solution to dryness under reduced pressure. Add water, collect the product in ether, and after this work up in the usual manner, recrystallize from a mixture of ether and pentane to obtain 13β-ethyl-17β-hydroxy-gon-4-en-3-one; ultraviolet absorption peak at 240 mμ (ε 15,500); infrared absorption peaks at 2.94, 6.06, 6.23.

Workup

  1. customevaporate the solution to dryness under reduced pressure
  2. customAdd water, collect the product in ether
  3. customafter this work up in the usual manner, recrystallize from a mixture of ether and pentane

Sources & evidence

ORD record
ord-91b320a214d847e38b73ca5384ed8548
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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