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

HRID 1077183

Reaction equation

HRID 1077183 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-ethyl-gon-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 (ε15,500); 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-70e82a9a7b6c4eb182668a24c63b2011
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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