Water → 2-[2-[(3-Methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

HRID 377299Notes

Reaction equation

HRID 377299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]([O:18][CH:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=O)[CH:6]=[CH:7][CH:8]=1.C([O-])(=O)C.[NH4+:38].O.ClCCl>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]2[O:18][C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:38]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 517165Ammonium AcetateHCID 542348532-Oxo-1,2-diphenylethyl 2-[(3-methoxy-phenyl)methyl]cyclohexanecarboxylate

Product 1

HCID 193584162-[2-[(3-Methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazoleYield 93.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-oxo-1,2-diphenylethyl 2-[(3-methoxy-phenyl)methyl]cyclohexanecarboxylate (440 mg) and ammonium acetate (593 mg) in acetic acid (2.4 ml) was refluxed for 3 hours and cooled to room temperature, and a mixture of water and dichloromethane was added thereto. The organic layer was washed with water and sodium bicarbonate aqueous solution, dried over magnesium sulfate, and evaporated in vacuo to afford 2-[2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole (394 mg).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and sodium bicarbonate aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-30e180bced7d4a37807ea11899456731
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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