Dimethylformamide → Ethyl 3-chloro-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate
Reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[Cl:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=1[OH:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=1[O:26][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8])[C:18]([O:20][CH2:21][CH3:22])=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (8.0 g), ethyl 3-chloro-4-hydroxybenzoate (7.38 g), potassium carbonate (5.09 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration and dried to give ethyl 3-chloro-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate as brown crystals (9.90 g, yield 74%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 145-146° C.
Workup
- filtrationthe precipitated crystals were collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-992b260e0d794063ace142fd8a12a617
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
Loading…