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

HRID 630293Notes

Reaction equation

HRID 630293 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 27629953-Chloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12742466(3-Chloropyridin-4-yl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 3-chloropyridine-4-carbaldehyde (1.08 g, 7.5 mmol) in anhydrous methanol (75 mL) was added sodium borohydride (405 mg, 10.7 mmol). The reaction mixture was stirred at room temperature for 1.5 hours. Water (75 mL) was added, and the reaction mixture was evaporated. The resultant residue was extracted with EtOAc (3×50 mL). The organic extracts were combined, washed with brine (2×100 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (3-chloropyridin-4-yl)methanol (1.0 g, 96%). The product was used in the next step without further purification.

Workup

  1. customthe reaction mixture was evaporated
  2. extractionThe resultant residue was extracted with EtOAc (3×50 mL)
  3. washwashed with brine (2×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0a7118d7ebd04760ac542c26bd01f4f7
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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