Ethyl bromoacetate → trans-1-[(3-Ethoxycarbonylmethoxyphenyl)methyl]-2-(4,5-diphenyloxazol-2-yl)cyclohexane

HRID 377325Notes

Reaction equation

HRID 377325 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[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)[CH:5]=[CH:6][CH:7]=1.Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[CH2:37]([O:36][C:34]([CH2:33][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]2[O:16][C:17]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1)=[O:35])[CH3:38]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 193584962-[2-[(3-Hydroxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazole

Product 1

HCID 54115607trans-1-[(3-Ethoxycarbonylmethoxyphenyl)methyl]-2-(4,5-diphenyloxazol-2-yl)cyclohexane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[2-[(3-hydroxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazole (320 mg), ethyl bromoacetate (0.13 ml), and potassium carbonate (270 mg) in acetonitrile (3.0 ml) was stirred at room temperature overnight and a mixture of ethyl acetate and water was added thereto. The organic layer was separated, washed with water (twice) and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed over silica gel using n-hexane--ethyl acetate as an eluent. The first eluate gave cis- or trans-1-[(3-ethoxycarbonylmethoxyphenyl)methyl]-2-(4,5-diphenyloxazol-2-yl)cyclohexane (isomer A) (79 mg) as a powder.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water (twice) and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-7c27b64f7893413494750ccdc4b68081
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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