Diethyl Ether → HCID 22790388, compound

HRID 1415019Notes

Reaction equation

HRID 1415019 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:23])=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH2:2][CH2:3][CH3:4].[C:24]1([CH2:30][CH2:31][C:32](Cl)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCOCC>N1C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[O:23][C:32](=[O:33])[CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 64801Benzenepropanoyl chlorideHCID 68145884HCID 68145884, compound

Product 1

HCID 22790388HCID 22790388, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Procedure

Cool 13β-butyl-17β-hydroxy-gon-4-en-3-one (0.10 g.) in pyridine (0.3 cc.) to -20° and add 3-phenylpropionyl chloride (0.10 g.) in benzene (0.3 cc.). Stir the mixture at -10° for 16 hours, add ice-cold water, ether (15 cc.) and benzene (15 cc.). Separate the organic layers and wash in turn with 2N sodium hydroxide solution, water and brine, and dry. Evaporate the solvent to an uncrystallizable gum, and take up in a little benzene and filter through neutral alumina (5 g.), then wash with more benzene. Evaporate the resulting benzene solution to obtain the title compound as a gum (0.085 g.); infrared absorption peaks at 5.78, 5.99, 13.3, 14.3 μ, with no absorption due to hydroxyl.

Workup

  1. customSeparate the organic layers
  2. washwash in turn with 2N sodium hydroxide solution, water and brine
  3. customdry
  4. customEvaporate the solvent to an uncrystallizable gum
  5. filtrationfilter through neutral alumina (5 g.)
  6. washwash with more benzene
  7. customEvaporate the resulting benzene solution

Sources & evidence

ORD record
ord-fa67d0b761224ad29537ba8afea9fedb
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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