Water → (5-(Benzyloxy)-6-chloropyridin-3-yl)methanol

HRID 709776Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([Cl:19])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14](OC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:13]([CH2:14][OH:15])[CH:12]=[N:11][C:10]=1[Cl:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of methyl 5-(benzyloxy)-6-chloronicotinate (3.00 g) in ethanol (40 mL) was added sodium tetrahydroborate (1.02 g), and the mixture was stirred at 60° C. for 3 hr. Water was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.76 g) as a colorless solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-36cf3a47caf842aab0b359dfa59a27e2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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