Ethanol → (3-Chloropyridin-4-yl)methanol

HRID 2401702Notes

Reaction equation

HRID 2401702 reaction equation
[Cl:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(O)C.[BH4-].[Na+]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Procedure

To a mixture of 1.53 g of 3-chloroisonicotinaldehyde and 5 ml of ethanol was gradually added 0.40 g of sodium borohydride under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour, and subsequently at room temperature for 1 hour. Saturated brine was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.40 g of (3-chloropyridin-4-yl)methanol.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1cfaa679637c436e9665911fc57648dd
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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