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

HRID 271471Notes

Reaction equation

HRID 271471 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 saturated aqueous NaCl, 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 saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5aa8bee118d34a868ffc042a76eeb027
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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