Sodium borohydride → (3,4-Difluoro-2-pyridinyl)methanol

HRID 522602Notes

Reaction equation

HRID 522602 reaction equation
[F:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866916052-Pyridinecarboxaldehyde, 3,4-difluoro-

Product 1

HCID 68277928(3,4-Difluoro-2-pyridinyl)methanolYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 5 (142 mg, 0.992 mmol) was dissolved in ethanol (5 mL) under N2(g) atmosphere. Sodium borohydride (ALDRICH, 113 mg, 2.98 mmol) was added and mixture of reaction was stirred for 1 hour. Crude of reaction was partitioned between DCM (15 mL) and distilled water (15 mL). Aqueous layer was extracted with DCM (2×15 mL). Organic layers were dried over MgSO4(anh), filtered and concentrated to yield title compound (3,4-difluoro-2-pyridinyl)methanol (140 mg, 0.965 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.37-8.40 (m, 1H), 7.50-7.55 (m, 1H), 5.45 (t, 1H), 4.61-4.63 (m, 2H). [ES+MS] m/z 146 (MH+).

Workup

  1. additionmixture of reaction
  2. customCrude of reaction
  3. customwas partitioned between DCM (15 mL)
  4. distillationdistilled water (15 mL)
  5. extractionAqueous layer was extracted with DCM (2×15 mL)
  6. dry with materialOrganic layers were dried over MgSO4(anh)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-550ec0761c9e420492ff068cf454994a
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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