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

HRID 2401704Notes

Reaction equation

HRID 2401704 reaction equation
[F:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(O)C.[BH4-].[Na+]>O>[F: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 1.2 g of 3-fluoroisonicotinaldehyde and 5 ml of ethanol was gradually added 0.36 g of sodium borohydride under ice-cooling, and the mixture was stirred under ice-cooling for 3 hours. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with saturated brine and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.12 g of (3-fluoropyridin-4-yl)methanol.

Workup

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

Sources & evidence

ORD record
ord-7cc93218c479482eac1e763c530609b2
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

Loading…