Ammonium Chloride → (2-Fluoropyridin-4-yl)methanol

HRID 426115Notes

Reaction equation

HRID 426115 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9]C(=O)C2C=CC=CC=2)[CH:5]=[CH:4][N:3]=1.C[O-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 59184859Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester

Product 1

HCID 11332468(2-Fluoropyridin-4-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester (36) (4.536 g, 19.62 mmol) in anhydrous methanol (40 ml) cooled in an ice bath, was added sodium methoxide (1.06 g, 19.62 mmol). After stirring for 30 min., excess ammonium chloride was added to the mixture. The mixture was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1)) to afford 2.34 g (94%) of a white solid; m.p. 70-71° C.; 1H NMR (200 MHz, CDCl3) δ: 2.40 (1H, t, J=4.0 Hz), 4.78 (2H, d, J=4 Hz), 6.97 (1H, s), 7.15 (1H, m), 8.15 (1H, d, J=5.0 Hz); m/z (EI): 127 (M+).

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1))

Sources & evidence

ORD record
ord-b4574048148042e19bb0004a53661a7d
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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