Benzenepropanoyl chloride → HCID 22790394, compound

HRID 1077196Notes

Reaction equation

HRID 1077196 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].[C:22]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:21][C:30](=[O:31])[CH2:29][CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 22790394HCID 22790394, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Add 13β-ethyl-17β-hydroxy-gon-4-en-3-one (0.11 g.) in dry pyridine (0.35 cc.) at -20° to 3-phenylpropionyl chloride (0.11 g.) in benzene (0.3 cc.). Keep this at -10° for 16 hours, add ice-cold water and extract with a mixture of equal volumes of ether and benzene. Wash the extracts in turn with 2N potassium hydroxide solution, water, 2N hydrochloric acid solution, and brine, and dry. Evaporate solvent to give a residue and recrystallize from a mixture of ether and ethyl acetate to obtain the title compound (0.10 g.), m.p. 135°-40°; infrared absorption peaks at 5.81, 5.99, 8.51, 13.3, 14.3 μ, showing no absorption due to hydroxyl.

Workup

  1. customat -10°
  2. customfor 16 hours
  3. additionadd ice-cold water
  4. extractionextract with a mixture of equal volumes of ether and benzene
  5. washWash the extracts in turn with 2N potassium hydroxide solution, water, 2N hydrochloric acid solution, and brine
  6. customdry
  7. customEvaporate solvent to give a residue
  8. customrecrystallize from a mixture of ether and ethyl acetate

Sources & evidence

ORD record
ord-213f77ecba144d2fba4a0f46ca28f3d7
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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