Diethyl Ether → 1-(4-Dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanone

HRID 2063744Notes

Reaction equation

HRID 2063744 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][N:24]([CH3:47])[C:25]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:30][CH2:29][CH:28]([CH:31]([OH:40])[CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:27][CH2:26]1.C(OCC)C>C(Cl)Cl>[CH3:23][N:24]([CH3:47])[C:25]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:30][CH2:29][CH:28]([C:31](=[O:40])[CH2:32][O:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 442519591-(4-Dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanol

Product 1

HCID 668865181-(4-Dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 15% solution of Dess-Martin periodinane in methylene chloride (22.9 g, 8.10 mmol) was added to a solution of 1-(4-dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanol (800 mg, 2.35 mmol) in anhydrous methylene chloride (25 ml). The mixture was stirred at room temperature for 4 h and then at 40° C. for 1.5 h and diethyl ether (100 ml) was then added. The suspension was washed with 25% potassium carbonate solution, 5% sodium bicarbonate solution, 1 M sodium thiosulfate solution and water (50 ml of each). The organic phase was dried with sodium sulfate and concentrated i. vac.

Workup

  1. waitat 40° C. for 1.5 h
  2. washThe suspension was washed with 25% potassium carbonate solution, 5% sodium bicarbonate solution, 1 M sodium thiosulfate solution and water (50 ml of each)
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated i

Sources & evidence

ORD record
ord-68b5af1d668c4fef82c9329c55517ad9
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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