Ammonium Hydroxide → (2-Methylpyridin-4-yl)methanol

HRID 426240Notes

Reaction equation

HRID 426240 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9]C(=O)C)[CH:5]=[CH:4][N:3]=1.[OH-].[NH4+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 54454664Acetic acid 2-methyl-pyridin-4-ylmethyl ester

Product 1

HCID 9942144(2-Methylpyridin-4-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 2-methyl-pyridin-4-ylmethyl ester (5.1 g, 31 mmol) was stirred with ammonium hydroxide (10 ml) in methanol (25 ml) at room temperature. After 24 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA) to afford 3.56 g (94%) of (2-methyl-pyridin-4-yl)-methanol as a pale yellow solid. m.p. 58-59° C. 1H NMR (200 MHz, CDCl3) δ 2.45 (3H, s), 4.66 (2H, s), 7.06 (1H, d, J=5.2 Hz), 7.14 (1H, s), 8.25 (1H, d, J=5.2 Hz).

Workup

  1. custom, the mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA)

Sources & evidence

ORD record
ord-a78655546bad438699a76c9697eebc01
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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