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

HRID 1585012Notes

Reaction equation

HRID 1585012 reaction equation
[Na].[Cl:2][C:3]1[N:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[OH2:11]>>[Cl:2][C:3]1[C:4]([CH2:5][OH:11])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 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 horohydride 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-71f4ff974668433fb0e9bb04a6f0aa64
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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