Acetate → (5-Methylpyridin-2-yl)methanol

HRID 369652Notes

Reaction equation

HRID 369652 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]=1

Participants

6

Reactant 4

HCID 175AcetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 123253842-Pyridinemethanol, 5-methyl-, 2-acetate

Product 1

HCID 12325387(5-Methylpyridin-2-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

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

  1. temperatureThe mixture was heated
  2. customnormally 1 hour
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane (3×50 mL)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b971476841dd4042aa7782cc9397a8e2
Source dataset
uspto-grants-2000_10
Patent number
US06140294

Reaction notes

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