Dimethylformamide → HCID 68883401, compound
Reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=1)[O:8][CH2:9][C:10]1[N:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13][C:14]=1[CH3:15].[OH:25][C:26]1[CH:27]=[C:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:24][O:23][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][O:25][C:26]2[CH:27]=[C:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:29]=[CH:30][CH:31]=2)=[CH:22][C:7]=1[O:8][CH2:9][C:10]1[N:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13][C:14]=1[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-(5-chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazole (400 mg), methyl 3-hydroxyphenylacetate (195 mg), potassium carbonate (320 mg) and N,N-dimethylformamide (10 mL) was stirred at 90° C. for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals of methyl 3-[4-methoxy-3-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]phenylacetate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals (470 mg, 85%). melting point: 88-89° C.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-224e8ef3938042b09baf56f76dd1ef1c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238716B2
Reaction notes
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