Water → 2-Bromo-1-(4,5-diphenyl-2-oxazolyl)cyclohexanol

HRID 377312Notes

Reaction equation

HRID 377312 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([C:15]2[O:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1.[OH2:32]>CS(C)=O>[Br:1][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:9]1([C:15]1[O:16][C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:19]=1)[OH:32]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 184591392-(1-Cyclohexenyl)-4,5-diphenyloxazole

Product 1

HCID 193585162-Bromo-1-(4,5-diphenyl-2-oxazolyl)cyclohexanolYield 38.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-Bromosuccinimide (2.64 g) was added to a stirred suspension of 2-(1-cyclohexenyl)-4,5-diphenyloxazole (3.00 g) in dimethyl sulfoxide (20 ml) and water (267 mg) at room temperature and the resulting mixture was stirred at the same temperature for 19 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography to afford 2-bromo-1-(4,5-diphenyl-2-oxazolyl)cyclohexanol (1.52 g) as a yellow solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fb85258373cd40faafa4741db5456fba
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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