Ethanol → [2-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[N:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].O1CCCC1.C(O)C.[BH4-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:12][CH:13]=[CH:14][N:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde (620 mg), tetrahydrofuran (10 ml) and ethanol (10 mL) was added sodium borohydride (54 mg) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (615 mg, 99%) of [2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol. The crystals were recrystallized from ethyl acetate-hexane. melting point: 143-144° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-91538a24d1a64eba8874a8125d329815
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238716B2
Reaction notes
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