Water → HCID 22790404, compound

HRID 1415020Notes

Reaction equation

HRID 1415020 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@:16]12[CH2:24][CH2:23][C@@H:22]3[C@@H:25]4[C:30]([CH2:31][CH2:32][C@H:21]3[C@@H:20]1[CH2:19][CH2:18][C@@H:17]2[OH:34])=[CH:29][C:28](=[O:33])[CH2:27][CH2:26]4)[CH:13]([CH3:15])[CH3:14].O>C1C=CC=CC=1.N1C=CC=CC=1>[CH2:12]([C@:16]12[CH2:24][CH2:23][C@@H:22]3[C@@H:25]4[C:30]([CH2:31][CH2:32][C@H:21]3[C@@H:20]1[CH2:19][CH2:18][C@@H:17]2[O:34][C:9](=[O:10])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:29][C:28](=[O:33])[CH2:27][CH2:26]4)[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 64801Benzenepropanoyl chlorideHCID 68143785HCID 68143785, compound

Product 1

HCID 22790404HCID 22790404, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Add 3-phenylpropionyl chloride (0.5 g.) in benzene (1.5 cc.) with swirling to 13β-isobutyl-17β-hydroxy-gon-4-en-3-one (0.5 g.) in pyridine (2 cc.) at -20°. Store the mixture at -10° for 18 hours, add water and extract the product with ether. Wash, dry and evaporate the extracts to give a residue and recrystallize from methanol to give the title compound, m.p. 101°-106°; ultraviolet absorption peak at 240 mμ (ε15,300); infrared absorption peaks at 5.75, 5.95 μ.

Workup

  1. extractionextract the product with ether
  2. washWash
  3. customdry
  4. customevaporate the extracts
  5. customto give a residue
  6. customrecrystallize from methanol

Sources & evidence

ORD record
ord-9e69f240c9e840869eff2142450e3b26
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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