Sodium borohydride → 2,2-Difluoro-2-(pyridin-2-YL)ethanol

HRID 398363

Reaction equation

HRID 398363 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([F:14])([F:13])[C:8](OCC)=[O:9].[BH4-].[Na+]>CO>[F:14][C:7]([F:13])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:8][OH:9]

Participants

4

Reactant 2

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

Product 1

HCID 99422162,2-Difluoro-2-(pyridin-2-YL)ethanolYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. stirred solution of 3.97 g (19.7 mmol) of ethyl 2-pyridyldifluoroacetate (prepared according to T. Taguchi, et al., Tetrahedron Lett. 1986, 27, 6103) in 40 mL of methanol was added 757 mg (20 mmol) of sodium borohydride in several portions. After stirring for 0.5 h, the cold bath was removed, and stirring continued another 0.5 h. The reaction was quenched with 2M HCl, and the solvents removed under reduced pressure. The residue was partitioned between ether and 10% Na2CO3, the aqueous layer extracted with several portions of ether and the combined organic layers washed with brine, dried over MgSO4 and the solvents removed to give 2.97 g of a yellow oil that was chromatographed on 65 g of fine SiO2 using 99:1 to 97:3 CH2—Cl2-CH3OH to give the title compound as an almost colorless solid:

Workup

  1. customthe cold bath was removed
  2. stirringstirring
  3. waitcontinued another 0.5 h
  4. customThe reaction was quenched with 2M HCl
  5. customthe solvents removed under reduced pressure
  6. customThe residue was partitioned between ether and 10% Na2CO3
  7. extractionthe aqueous layer extracted with several portions of ether
  8. washthe combined organic layers washed with brine
  9. dry with materialdried over MgSO4
  10. customthe solvents removed

Sources & evidence

ORD record
ord-fbb7bc7d9a0c4de29ad245df296d9c27
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Linked notes

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