Acetate → (5-Methylpyridin-2-yl)methanol
Reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)(=O)C.C(N(CC)CC)C.C(OCC)(=O)C.C([O-])(=O)C>Cl>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Acetoxymethyl-5-methyl pyridine (30 g, 182 mmol) was dissolved in hydrochloric acid (100 mL, 4 N). The mixture was heated under reflux, until TLC (silica gel; triethylamine:ethyl acetate:petroleum ether 40-60=1:9:19) showed complete absence of the acetate (normally 1 hour). The mixture was cooled, brought to pH>11, extracted with dichloromethane (3×50 mL) and the solvent removed in vacuo. Pure 2-hydroxymethyl-5-methyl pyridine (18.80 g, 152 mmol, 84%) was obtained by Kugelrohr distillation (p=20 mm Hg, T=130° C.) as a slightly yellow oil.
Workup
- temperatureThe mixture was heated
- customnormally 1 hour
- temperatureThe mixture was cooled
- extractionextracted with dichloromethane (3×50 mL)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-f24681b1ecbd4719bae7e01f2268f1f7
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06242409B1
Reaction notes
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