[BH4-].[Na+].[F:3][CH:4]([F:18])[O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=[O:17]>CCO.O>[F:3][CH:4]([F:18])[O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][OH:17]NaBH4 (255 mg, 6.73 mmol) was added to a suspension of 2-(difluoromethoxy)-1-naphthaldehyde (0.997 g, 4.49 mmol) in EtOH (29.9 mL). After 3 h the mixture was diluted with H2O, extracted with EtOAc, the combined extracts were washed with brine (200 mL), dried over Na2SO4, filtered, and the filtrate concentrated to give a residue that was purified by silica gel chromatography to provide (2-(difluoromethoxy)naphthalen-1-yl)methanol (387 mg, 39%) as an orange solid.
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