Sodium borohydride → 2,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanol

HRID 1987046Notes

Reaction equation

HRID 1987046 reaction equation
C([O:3][C:4](=O)[C:5]([F:14])([F:13])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)C.[BH4-].[Na+]>CCO>[F:14][C:5]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12035972Ethyl Difluoro(5-methylpyridin-2-yl)acetate

Product 1

HCID 577227102,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of difluoro-(5-methyl-pyridin-2-yl)-acetic acid ethyl ester (10.5 g, 0.05 mol), as prepared in the previous step, in EtOH (98 mL) cooled to 0° C. was added NaBH4 (3.7 g, 0.098 mol, 2×). After 3 h the reaction was carefully quenched with saturated NH4Cl (100 mL) and partitioned with EtOAc (200 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the product as a white solid (8.5 g, 0.05 mol, 100% crude yield). 1H NMR (300 Hz, CDCl3) δ 8.43 (s, 1H), 7.66 (m, 2H), 4.22 (t, J=12.3 Hz), 2.41 (s, 1H); LC/MS (m/z) [M+1]+ 174.1 (calculated for C8H10F2NO, 174.2).

Workup

  1. customAfter 3 h the reaction was carefully quenched with saturated NH4Cl (100 mL)
  2. custompartitioned with EtOAc (200 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bbc14616ef543899f0b56f1d025c39e
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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