Benzoyl chloride → 13beta-Propyl-17beta-benzyloxy-gon-4-en-3-one

HRID 1415017Notes

Reaction equation

HRID 1415017 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:22])=[CH:17][C:16](=[O:21])[CH2:15][CH2:14]4)[CH2:2][CH3:3].[C:23](Cl)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:17][C:16](=[O:21])[CH2:15][CH2:14]4)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 6814332113beta-Propyl-17beta-hydroxy-gon-4-en-3-one

Product 1

HCID 8673439513beta-Propyl-17beta-benzyloxy-gon-4-en-3-one

Procedure

Esterify 13β-propyl-17β-hydroxy-gon-4-en-3-one (2.5 g.) with benzoyl chloride (2.0 g.). Purify the product by chromatography on Florex and recrystallize from ethyl acetate to obtain the title compound, m.p. 198°-200°; ultraviolet absorption peak at 240 mμ (ε25,000); infrared absorption peaks at 5.84, 6.00 μ.

Workup

  1. customPurify the product by chromatography on Florex
  2. customrecrystallize from ethyl acetate

Sources & evidence

ORD record
ord-ecbba5d207a7486dbc23107e7066d6f4
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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