Ammonium Acetate → 2-[(4,5-Diphenyl-1,3-oxazol-2-yl)methyl]cyclohexan-1-one

HRID 1067116Notes

Reaction equation

HRID 1067116 reaction equation
C([O-])(=O)C.[NH4+:5].[O:6]=[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH2:13][C:14]([O:16][CH:17]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)=O>C(O)(=O)C>[C:20]1([C:18]2[N:5]=[C:14]([CH2:13][CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:7]3=[O:6])[O:16][C:17]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 53903505HCID 53903505, compound

Product 1

HCID 131268312-[(4,5-Diphenyl-1,3-oxazol-2-yl)methyl]cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ammonium acetate (6.3 g), acetic acid (30 ml) and 1,2-diphenyl-2-oxoethyl (2-oxocyclohex-1-yl)acetate (15.0 g) was heated under reflux for 2.5 hours. After used workup, the crude product was purified by column chromatography (silica gel 100 g, eluent; hexane:ethyl acetate=20:1 then 9:1 then 6:1) to give 2-[(4,5-diphenyl-oxazol-2-yl)methyl]cyclohexanone as an amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customthe crude product was purified by column chromatography (silica gel 100 g, eluent

Sources & evidence

ORD record
ord-e19c89d4443c4c89b575181365b39763
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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