Dimethylformamide → HCID 10638429, compound

HRID 233294Notes

Reaction equation

HRID 233294 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 10638429HCID 10638429, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (9.2 g), p-hydroxyacetophenone (7.95 g), potassium carbonate (6.73 g) and N,N-dimethylformamide (DMF) (100 ml) was stirred for 2.5 hours at temperatures ranging from 70° to 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried (MgSO4), then the solvent was distilled off to give 4'-(5-methyl-2-phenyl-4-oxazolylmethoxy)acetophenone (11.6 g, 85%). Recrystallization from ethyl acetate--ether gave colorless prisms, m.p.126°-127° C.

Workup

  1. customranging from 70° to 80° C
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-57380fc5d8df46798d2fb82ae9d42ac4
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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