2-Pyridinemethanol, 2-acetate → Methanesulfonic acid pyridin-2-ylmethyl ester
Reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=O)C.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(N(CC)CC)C>[CH3:12][S:13]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:15])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Methylpyridine of general structure III is prepared by α-methylation of substituted pyridine II using the method of Kray and Reinecke (J. Am. Chem. Soc., 1964, 86, 5355). Oxidation with m-chloroperbenzoic acid gives substituted 2-methylpyridine N-oxide IV. Treatment of the latter with phosphoryl chloride gives the 2-chloromethyl substituted pyridine VII. Alternatively, refluxing IV in acetic anhydride gives the 2-(acetoxymethyl) pyridine VII which is hydrolysed with aqueous base to the corresponding alcohol VII. When this hydroxymethyl derivative is treated with methanesulfonyl chloride in the presence of triethylamine, the 2-(methanesulfonyloxymethyl)pyridine is obtained, whereas treatment with brominetriphenylphosphine gives the 2-(bromomethyl)pyridine VII. When either the bromomethyl, chloromethyl, or the mesyloxymethyl pyridine derivative VII is refluxed in acetonitrile in the presence of triphenylphosphine, the corresponding phosphonium salt VIII is formed.
Sources & evidence
- ORD record
- ord-e4374a75a1334a3ebc8690eac755be30
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05506227
Reaction notes
Loading…