2-(DIFLUOROMETHOXY)-1-NAPHTHALDEHYDE → [2-(Difluoromethoxy)naphthalen-1-yl]methanol

HRID 1055422Notes

Reaction equation

HRID 1055422 reaction equation
[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]

Participants

5

Reactant 2

HCID 8181662-(DIFLUOROMETHOXY)-1-NAPHTHALDEHYDEHCID 4311764Sodium borohydride

Product 1

HCID 43394581[2-(Difluoromethoxy)naphthalen-1-yl]methanolYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined extracts were washed with brine (200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give a residue that
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-331b8d17532b4ac585ee90dc9feafdcb
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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