Decanoyl chloride → (8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoate

HRID 1077192

Reaction equation

HRID 1077192 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:13]([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)[CH3:14]>N1C=CC=CC=1.Cl>[CH2:13]([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:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:28][C:27](=[O:32])[CH2:26][CH2:25]4)[CH3:14]

Participants

5

Reactant 2

HCID 66982Decanoyl chlorideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 44626081(8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoateYield 50.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Add decanoyl chloride (1.9 g.) to 13β-ethyl-17β-hydroxy-gon-4-en-3-one (1.3 g.) in pyridine (12.5 cc.) and allow the mixture to stand at room temperature overnight. Pour the mixture in 2N hydrochloric acid and extract with ether. Wash, dry and evaporate the extracts and recrystallize the residue from benzene-hexane to give the title compound (1.0 g.), m.p. 97°-97.5°; ultraviolet absorption peak at 239 mμ (ε16,500); infrared absorption peaks at 5.74; 5.99, 6.17 μ.

Workup

  1. extractionextract with ether
  2. washWash
  3. customdry
  4. customevaporate the extracts
  5. customrecrystallize the residue from benzene-hexane

Sources & evidence

ORD record
ord-26ff28a40a344a6a84d5c76a985b2805
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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