Sodium borohydride → 2-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-

HRID 2207567

Reaction equation

HRID 2207567 reaction equation
[BH4-].[Na+].[F:3][CH:4]([F:18])[O:5][CH2:6][C:7]1[N:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[CH:9][CH:8]=1>CCO>[F:18][CH:4]([F:3])[O:5][CH2:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66718372Ethyl 6-difluoromethoxymethylpyridine-2-carboxylate

Product 1

HCID 667184182-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-Yield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

NaBH4 (377 mg, 9.96 mmol) was added to a solution of ethyl 6-difluoromethoxymethylpyridine-2-carboxylate (2.30 g, 9.96 mmol) in EtOH (50 mL) at 0° C., the mixture was warmed to 80° C. and stirred for 5 h. The mixture was cooled to 0° C., quenched with sat. aq. NH4Cl, concentrated in vacuo and partitioned between EtOAc and brine. The organic layer was separated, dried (MgSO4), filtered and evaporated to give the title compound (1.50 g, 80%) as a colorless oil; NMR δH (400 MHz, CDCl3) 7.73 (1H, t, J 8.0 Hz), 7.35 (1H, d, J 8.0 Hz), 7.19 (1H, d, J 8.0 Hz), 6.39 (1H, t, J 74.0 Hz), 5.02 (2H, s), 4.76 (2H, s); (M+H)+ 190.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and brine
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7f3e90bb013f4afda2e16b5db8d072c3
Source dataset
uspto-grants-2016_06
Patent number
US09376443B2

Linked notes

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