Ethyl Acetate → 2-[2-[(3-Hydroxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazole

HRID 377300Notes

Reaction equation

HRID 377300 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[C:20]2[O:21][C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH:10]=[CH:11][CH:12]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[C:20]2[O:21][C:22]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:24]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 193584162-[2-[(3-Methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

Product 1

HCID 193584962-[2-[(3-Hydroxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazoleYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 M Solution of boron tribromide in dichloromethane (1.25 ml) was added dropwise to a stirred solution of 2-[2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole (370 mg) in dichloromethane (2.0 ml) under ice cooling. The resulting mixture was stirred at the same temperature for 2 hours and at room temperature for 22 hours, and then a mixture of ethyl acetate and sodium bicarbonate aqueous solution was added thereto. The organic layer was washed with sodium bicarbonate aqueous solution 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 to afford 2-[2-[(3-hydroxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazole (303 mg) as a syrup.

Workup

  1. additionwas added
  2. washThe organic layer was washed with sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-8a59e5ba56ce47769dbd4913b64b8dab
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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