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

HRID 2063718Notes

Reaction equation

HRID 2063718 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:23][CH:24]([CH:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:1]([O:3][CH:4]([O:23][CH:24]([CH:32]1[CH2:33][CH2:34][C:35](=[O:38])[CH2:36][CH2:37]1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 214336324-(1-Hydroxy-2-phenylethyl)cyclohexanone

Product 1

HCID 668875294-[1-(1-Ethoxy-ethoxy)-2-phenylethyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl vinyl ether (998 mg, 1.32 ml, 13.8 mmol) and pyridinium tosylate (44 mg, 0.17 mmol) were added to a solution of 4-(1-hydroxy-2-phenylethyl)cyclohexanone (2.52 g, 11.5 mmol) in anhydrous methylene chloride (50 ml) and the mixture was stirred at room temperature overnight. Methylene chloride (20 ml) was added to the mixture and the mixture was washed with water, 5% sodium bicarbonate solution and sodium chloride solution (50 ml of each). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

Workup

  1. washthe mixture was washed with water, 5% sodium bicarbonate solution and sodium chloride solution (50 ml of each)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated i

Sources & evidence

ORD record
ord-8c79fd8dea9c466884db519ac85f7bf5
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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