Water → (4-(Benzyloxy)-3-fluorophenyl)methanol

HRID 901164

Reaction equation

HRID 901164 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C.O>C(O)C.C1COCC1>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde

Product 1

HCID 21976875(4-(Benzyloxy)-3-fluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (500 mg, 13.2 mmol) was added to a solution of 4-benzyloxy-3-fluoro-benzaldehyde (CAB03016, 7.32 g, 31.8 mmol) in ethanol (40 mL) and THF (40 mL) at 0° C. The clear and colourless solution was allowed to warm to room temperature and stirred for 12 h at this temperature. Ethyl acetate (150 mL) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×50 mL) and brine (50 mL), dried over sodium sulphate and concentrated under reduced pressure. The white solid residue was dissolved in dichloromethane and precipitated by addition of hexane. The white powder was filtered off and dried under high vacuum. Yield: 7.16 g (97%). 1H-NMR (400 MHz, CDCl3) δ=1.71 (s, 1H, —OH), 4.61 (s, 2H, —CH2OH), 5.15 (s, 2H), 6.97 (dd, J=8.6, 8.6 Hz, 1H), 7.02 (dd, J=8.6, 1.9 Hz, 1H), 7.13 (dd, J=11.7, 1.9 Hz, 1H), 7.30-7.46 (m, 5H). LRMS (FAB+): 91 (100), 215.1 (40), 232.1 (100, [M]+).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe white solid residue was dissolved in dichloromethane
  6. customprecipitated by addition of hexane
  7. filtrationThe white powder was filtered off
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-4843ceb8c5be403ebc3149f79c348677
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Linked notes

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