Water → (2-Chloropyridin-3-yl)methanol

HRID 249492Notes

Reaction equation

HRID 249492 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl.[OH2:12]>>[Cl:3][C:4]1[C:5]([CH2:6][OH:12])=[CH:8][CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 115283992-Chloro-3-chloromethyl-pyridine

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanol

Procedure

In 100 ml of cold water was dissolved 8.98 g of sodium borohydride and with ice-cooling and stirring, 11.7 g (0.0665 mole) of 2-chloronicotinyl chloride was added in small portions. The mixture was further stirred at the same temperature for 30 minutes and, then, extracted with Et2O (100 ml×3). The extract was dried over MgSO4 and distilled to remove Et2O. The procedure gave 8.75 g of (2-chloro-3-pyridyl)methanol as a pale yellow oil. When left standing at room temperature, this product solidified thoroughly.

Workup

  1. temperaturewith ice-cooling
  2. stirringThe mixture was further stirred at the same temperature for 30 minutes
  3. extractionextracted with Et2O (100 ml×3)
  4. dry with materialThe extract was dried over MgSO4
  5. distillationdistilled
  6. customto remove Et2O

Sources & evidence

ORD record
ord-a5c845deb79b4fd6949a8c832bd0028f
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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