Acetic Anhydride → Acetic acid 2-methyl-pyridin-4-ylmethyl ester

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=1[O-].[C:10]([O:13]C(=O)C)(=[O:12])[CH3:11]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:13][C:10](=[O:12])[CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 707332,4-Dimethylpyridine 1-oxide

Product 1

HCID 54454664Acetic acid 2-methyl-pyridin-4-ylmethyl esterYield 15%

Procedure

2,4-Dimethyl-pyridine 1-oxide (24.6 g, 0.2 mol) was stirred in acetic anhydride (200 ml) in an oil bath (140-150° C.) for 4 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (2:1)) to afford 5.1 g (15%) of acetic acid 2-methyl-pyridin-4-ylmethyl ester as a colorless oil. 1H NMR (200 MHz, CDCl3) δ 2.15 (3H, s), 2.56 (3H, s), 5.08 (2H, s), 7.05 (1H, d, J=5.0 Hz), 7.11 (1H, s), 8.48 (1H, d, J=5.0 Hz).

Workup

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

Sources & evidence

ORD record: ord-7b3db77091394d858e625dd6d0bc163b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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