Potassium Carbonate → 2-(1,2-Epoxycyclohexyl)-4,5-diphenyloxazole

HRID 377313Notes

Reaction equation

HRID 377313 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([C:9]1[O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1)[OH:8].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:8]1[CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]12[C:9]1[O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 193585162-Bromo-1-(4,5-diphenyl-2-oxazolyl)cyclohexanol

Product 1

HCID 184591642-(1,2-Epoxycyclohexyl)-4,5-diphenyloxazoleYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-1-(4,5-diphenyl-2-oxazolyl)-cyclohexanol (120 mg) and potassium carbonate (83 mg) in N,N-dimethylformamide (0.3 ml) was stirred at room temperature for 6 hours and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo to afford 2-(1,2-epoxycyclohexyl)-4,5-diphenyloxazole (94 mg) as a pale yellow powder.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6f715285732440fca41c8f5f3e33e817
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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