Water → (3,5-Dichloropyridin-4-yl)methanol

HRID 629980Notes

Reaction equation

HRID 629980 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:12])[C:9]=1[CH:10]=[O:11].O>CO>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:12])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 17855219(3,5-Dichloropyridin-4-yl)methanolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (322 mg, 8.5 mmol) in anhydrous methanol (10 mL) was added a solution of 3,5-dichloropyridine-4-carbaldehyde (1.0 g, 5.7 mmol) in anhydrous methanol (5 mL) at 0° C. The mixture was stirred for 3 hours at room temperature. Water was added and extracted 3 times with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (3,5-dichloropyridin-4-yl)methanol was obtained (940 mg, 93% yield) and used for the next step without further purification; 1H NMR (400 MHz, CDCl3): δ 2.23 (t, J=7.1 Hz, 1H), 4.94 (d, J=7.1 Hz, 2H), 8.52 (s, 2H).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-15eff9b7be0c4c769352455ef6f0a1e5
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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