Diphenyl sulfide → 4-Benzyloxycarbonylmethylcyclohexanone ethylene acetal

HRID 516870

Reaction equation

HRID 516870 reaction equation
C1(SC2C=CC=CC=2)C=CC=CC=1.[O:14]1[C:18]2([CH2:23][CH2:22][C:21](=[CH:24][C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:20][CH2:19]2)[O:17][CH2:16][CH2:15]1.[H][H]>CO.[Pd].[C]>[O:14]1[C:18]2([CH2:23][CH2:22][CH:21]([CH2:24][C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])[CH2:20][CH2:19]2)[O:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 8766Diphenyl sulfideHCID 86102242HCID 86102242, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 590090264-Benzyloxycarbonylmethylcyclohexanone ethylene acetalYield 82%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Diphenyl sulfide (33 mg, 0.18 mmol) and 10% Pd-carbon (1.08 g) were added to a solution of benzyl 2-(1,4-dioxaspiro[4,5]decan-8-ylidene)acetate (5.0 g, 17.34 mmol) in methanol (50 ml) under a nitrogen gas stream, the atmosphere in the system was replaced five times with nitrogen gas, was then filled with hydrogen gas, followed by stirring under a hydrogen gas stream for 5 hr. The catalyst was removed by filtration through Celite pad and was washed with ethanol, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (4.1 g, yield 82%).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. washwas washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4bed41fc4ca41229e4ff853442293c1
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Linked notes

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