Sodium Hydroxide → [2-Methyl-5-(4-trifluoromethyl-phenyl)-furan-3-yl]-methanol
Reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.CCOCC.O>[CH3:1][C:2]1[O:3][C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:15][CH:16]=2)=[CH:5][C:6]=1[CH2:7][OH:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 23, 0.27 g) in tetrahydrofuran (10 ml) stirred at 0° C. under a nitrogen atmosphere was treated with 1M lithium aluminium hydride in ether (1.0 ml). The reaction mixture was stirred at this temperature for 4 hours and then water (2 ml) and 2M aqueous sodium hydroxide (2 ml) added. The reaction mixture was further diluted with water; extracted with ethyl acetate and the organic solution extracted with water and dried with brine and over sodium sulfate and concentrated. The product isolated after evaporation of the solvent was further purified by Biotage™ chromatography using a mixture of petroleum ether:ethyl acetate (1:1) as eluent to give the title compound as a white solid.
Workup
- extractionextracted with ethyl acetate
- extractionthe organic solution extracted with water
- dry with materialdried with brine and over sodium sulfate
- concentrationconcentrated
- customThe product isolated
- customafter evaporation of the solvent
- customwas further purified by Biotage™ chromatography
- additiona mixture of petroleum ether:ethyl acetate (1:1) as eluent
Sources & evidence
- ORD record
- ord-55af0c1fec17466ca50bb1b0a293d948
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091237B2
Reaction notes
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