Hydrochloric Acid → 3-Pyridinemethanol, 6-(chlorodifluoromethyl)-alpha-methyl-

HRID 2388254Notes

Reaction equation

HRID 2388254 reaction equation
[Cl:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]([F:12])([F:13])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59218618Ethanone, 1-[6-(chlorodifluoromethyl)-3-pyridinyl]-

Product 1

HCID 592186063-Pyridinemethanol, 6-(chlorodifluoromethyl)-alpha-methyl-Yield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{6-[chloro(difluoro)methyl]pyridin-3-yl}ethanone (B) (0.85 g, 4.14 mmol) in MeOH (10 mL) at 0° C. was added NaBH4 (0.16 g, 4.14 mmol). The mixture was stirred for 30 min and 2 M HCl aqueous solution was added until pH reached 7. Solvent was removed under reduced pressure and the remaining mixture was extracted with CH2Cl2 (2×50 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated, and dried in vacuo to give 0.798 g of analytically pure 1-{6-[chloro(difluoro)methyl]-pyridin-3-yl}ethanol (C) on GC-MS as a light yellow oil in 93% yield. GC-MS: mass calcd for C8H6ClF2NO [M]+ 207. Found 207.

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionthe remaining mixture was extracted with CH2Cl2 (2×50 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-dc81afd64dc94ff091ba3b4fb49f2515
Source dataset
uspto-grants-2012_09
Patent number
US08269016B2

Reaction notes

Loading…