3-Hydroxybenzyl alcohol → (3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol
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].[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:16]=[C:17]([CH2:18][OH:19])[CH:20]=[CH:21][CH:22]=2)[N:4]=1Participants
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 (22.3 g), 3-hydroxybenzyl alcohol (10.0 g), potassium carbonate (11.14 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 4 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:1, v/v) to give (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol as colorless crystals (12.75 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 100-101° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- washeluted with ethyl acetate-hexane (1:1
Sources & evidence
- ORD record
- ord-b1eca34375a54c12a89819457556ad6d
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
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