Ethyl vinyl ether → 4-[1-(1-Ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanone

HRID 2063740Notes

Reaction equation

HRID 2063740 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH:18]([O:20][CH2:21][CH3:22])=[CH2:19].[OH:23][CH:24]([CH:33]1[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]1)[CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH2:18]([O:20][CH:21]([O:23][CH:24]([CH:33]1[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]1)[CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:22])[CH3:19]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 668872834-(1-Hydroxy-2-phenoxyethyl)cyclohexanone

Product 1

HCID 668868394-[1-(1-Ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium tosylate (15 mg, 0.06 mmol) and ethyl vinyl ether (339 mg, 450 μl, 4.70 mmol) were added to a solution of 4-(1-hydroxy-2-phenoxyethyl)cyclohexanone (919 mg, 3.92 mmol) in anhydrous methylene chloride (20 ml) and the mixture was stirred at room temperature overnight. Methylene chloride (20 ml) was then added to the mixture and the mixture was washed with water, 5% strength sodium bicarbonate solution and saturated sodium chloride solution (50 ml of each). The organic phase was dried with sodium sulfate and concentrated in vacuo.

Workup

  1. washthe mixture was washed with water, 5% strength sodium bicarbonate solution and saturated sodium chloride solution (50 ml of each)
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a742f5940691470d98519dd0cf2c3cb3
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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