Sodium borohydride → HCID 58443299, compound

HRID 1630751Notes

Reaction equation

HRID 1630751 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[CH:4][C:5]([C:8](OC)=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+]>CO.CCOC(C)=O.O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 58443263HCID 58443263, compound

Product 1

HCID 58443299HCID 58443299, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-chloro-4-(3-fluorophenyl)picolinate (0.196 g, 0.738 mmol) in MeOH (6 mL) was added NaBH4 (0.152 g, 4.02 mmol). The reaction mixture was stirred at rt for 10 min, and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (1×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 60% EtOAc in hexanes) gave (5-chloro-4-(3-fluorophenyl)pyridin-2-yl)methanol.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (1×)
  2. washthe combined organic extracts were washed with brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (10% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-88f6fa0060274dceb4b92ca153fb3cf1
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

Loading…