Water → (5-Chloropyridin-2-yl)methanol

HRID 2101414Notes

Reaction equation

HRID 2101414 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](OC)=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+].O.CCOC(C)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 11298216Methyl 5-chloropyridine-2-carboxylate

Product 1

HCID 20537893(5-Chloropyridin-2-yl)methanolYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of methyl 5-chloropicolinate (1 g, 5.8 mmol) in methanol at room temperature under argon was added sodium borohydride (440 mg, 11.57 mmol). The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was concentrated under vacuum to obtain a gum. Water (15 mL) and EtOAc (30 mL) were added and the layers were separated. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to obtain 840 mg of the title compound as colorless gum. HPLC/MS: retention time=0.755 min, [M+H]+=144.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto obtain a gum
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb5564ad3b0e4ad1b21b42f419c2a878
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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