Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[C:20]([CH3:21])=[C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=1)=O>C1COCC1>[CH2:23]([O:22][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[C:20]=1[CH3:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1Participants
Procedure
To a suspension of LiAlH4 (8.8 g, 235 mmol) in dry THF (120 mL) was added a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (25.4 g, 78.3 mmol) in THF (180 mL) dropwise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. After this time, the reaction mixture was cooled to 0° C. and quenched carefully by addition of cold water (10 mL) followed by 15% NaOH solution (10 mL) and additional water. The resulting solution was stirred for one hour, then filtered through a sintered glass funnel. The filter pad was washed with THF (50 mL). The combined filtrates were dried over Na2SO4, filtered, and concentrated to afford (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (21.5 g, 92%, crude) as a white solid. The crude product was used in the next step without further purification. MS calcd. for C19H16FO2 [(M−H)−] 295, obsd. 294.9.
Workup
- temperatureAfter this time, the reaction mixture was cooled to 0° C.
- customquenched carefully by addition of cold water (10 mL)
- stirringThe resulting solution was stirred for one hour
- filtrationfiltered through a sintered glass funnel
- washThe filter pad was washed with THF (50 mL)
- dry with materialThe combined filtrates were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-aba74ccc1768490792b66b82914c0185
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000044B2
Linked notes
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