Benzenepropanoyl chloride → 13beta-Propyl-17beta-(3-phenylpropionoxy)-gon-4-en-3-one

HRID 1077197Notes

Reaction equation

HRID 1077197 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([C@:15]12[CH2:23][CH2:22][C@@H:21]3[C@@H:24]4[C:29]([CH2:30][CH2:31][C@H:20]3[C@@H:19]1[CH2:18][CH2:17][C@@H:16]2[OH:33])=[CH:28][C:27](=[O:32])[CH2:26][CH2:25]4)[CH2:13][CH3:14]>C1C=CC=CC=1.N1C=CC=CC=1>[CH2:12]([C@:15]12[CH2:23][CH2:22][C@@H:21]3[C@@H:24]4[C:29]([CH2:30][CH2:31][C@H:20]3[C@@H:19]1[CH2:18][CH2:17][C@@H:16]2[O:33][C:9](=[O:10])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:28][C:27](=[O:32])[CH2:26][CH2:25]4)[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 6814332113beta-Propyl-17beta-hydroxy-gon-4-en-3-one

Product 1

HCID 2279042013beta-Propyl-17beta-(3-phenylpropionoxy)-gon-4-en-3-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Add 3-phenylpropionyl chloride (2.9 g.) in benzene (10 cc.) to 13β-propyl-17β-hydroxy-gon-4-en-3-one (2.5 g.) in pyridine at -10°. Pour the mixture into ice water and extract with benzene-ether. Wash, dry and evaporate the extracts to a gum and purify by chromatography upon Florex. Recrystallize from ethyl acetate-hexane to obtain the title compound, m.p. 104°-108°. Ultraviolet absorption peak at 240 mμ (ε16,000); infrared absorption peaks at 5.76, 6.00 μ.

Workup

  1. extractionextract with benzene-ether
  2. washWash
  3. customdry
  4. customevaporate the extracts to a gum
  5. custompurify by chromatography upon Florex
  6. customRecrystallize from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a51419fbb8814d1fb4e223aec13d665c
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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