Benzenepropanoyl chloride → HCID 22790394, compound

HRID 1415016Notes

Reaction equation

HRID 1415016 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-f5b80aac5c214053a8f7a88e4ee7f7e9
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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