Ethyl bromoacetate → Ethyl [3-[[2-(4,5-diphenyl-2-oxazolyl)-2-cyclohexen-1-yl]methyl]phenoxy]acetate

HRID 377327Notes

Reaction equation

HRID 377327 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]2[C:14]([C:15]3[O:16][C:17]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=3)=[CH:13][CH2:12][CH2:11][CH2:10]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+]>CN(C)C=O>[C:20]1([C:18]2[N:19]=[C:15]([C:14]3[CH:9]([CH2:8][C:4]4[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=4)[O:1][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:10][CH2:11][CH2:12][CH:13]=3)[O:16][C:17]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 193584952-[6-[(3-Hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole

Product 1

HCID 54289111Ethyl [3-[[2-(4,5-diphenyl-2-oxazolyl)-2-cyclohexen-1-yl]methyl]phenoxy]acetateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-[6-[(3-hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole (885 mg), ethyl bromoacetate (399 mg), and potassium carbonate (360 mg) in N,N-dimethylformamide was stirred at room temperature for 3 days and partitioned between ethyl acetate and water. The organic layer was separated, washed with water (twice) and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (n-hexane--ethyl acetate (20:1)) to afford ethyl [3-[[2-(4,5-diphenyl-2-oxazolyl)-2-cyclohexen-1-yl]methyl]phenoxy]acetate (847 mg) as a solid.

Workup

  1. custompartitioned between ethyl acetate and water
  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 purified by column chromatography on silica gel (n-hexane--ethyl acetate (20:1))

Sources & evidence

ORD record
ord-8a75ccde4e7b46b8aa46d4dda9861764
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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