Sodium borohydride → 2,2-Difluoro-2-(2-pyridyl)-1-methoxyethanol

HRID 1386802Notes

Reaction equation

HRID 1386802 reaction equation
[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:3]([O:5][CH2:6]C)=[O:4].[BH4-].[Na+]>CO>[F:14][C:2]([F:1])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH:3]([O:5][CH3:6])[OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10631894Ethyl difluoro(pyridin-2-yl)acetate

Product 1

HCID 181875122,2-Difluoro-2-(2-pyridyl)-1-methoxyethanolYield 108.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl difluoro(2-pyridyl)acetate (1.00 g, 4.97 mmol, from EXAMPLE 202, Step B) was dissolved in CH3OH (15 mL) in a 3-neck round bottom flask fitted with a mechanical stirrer, and the resulting solution was cooled in a dry iceli-PrOH bath. Sodium borohydride (114 mg, 3.0 mmol) was added in 2 portions 15 min. apart. After an additional 55 min., the cold reaction was quenched by the addition of saturated aq. NH4Cl (6.5 mL) over 12 min. After 10 min., the cooling bath was removed and the mixture was stirred for 35 min. before being diluted with saturated aq. NaCl (100 mL) and extracted with EtOAc (4×75 mL). The combined organic layers were dried (Na2SO4), decanted, and evaporated to give 1.02 g of crude 2,2-difluoro-2-(2-pyridyl)-1-methoxyethanol as an amber oil.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturethe resulting solution was cooled in a dry iceli-PrOH bath
  3. customthe cold reaction
  4. customwas quenched by the addition of saturated aq. NH4Cl (6.5 mL) over 12 min
  5. waitAfter 10 min.
  6. customthe cooling bath was removed
  7. additionbefore being diluted with saturated aq. NaCl (100 mL)
  8. extractionextracted with EtOAc (4×75 mL)
  9. dry with materialThe combined organic layers were dried (Na2SO4)
  10. customdecanted
  11. customevaporated

Sources & evidence

ORD record
ord-8326c5519a274a99bbce72723119fc17
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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