Methyl chloroformate → HCID 21561613, compound

HRID 1581132Notes

Reaction equation

HRID 1581132 reaction equation
Cl.[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:11])[C:7]([CH3:10])=[N:8][CH:9]=1.[C:12](Cl)(=[O:15])[O:13][CH3:14]>N1C=CC=CC=1>[CH3:14][O:13][C:12]([O:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:11])[C:7]([CH3:10])=[N:8][CH:9]=1)=[O:15]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 1991873-Pyridinemethanol, 5-hydroxy-6-methyl-, hydrochloride

Product 1

HCID 21561613HCID 21561613, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.8 g. of 5-hydroxymethyl-2-methyl-3-pyridinol hydrochloride in 10 ml. of pyridine was added 1.0 g. of methyl chlorocarbonate dropwise under cooling. After standing overnight, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give 1.0 g. of an oily substance. The oily substance was purified by column chromatography (silica gel 20 g.) and 0.6 g. of the desired product as colorless crystal was obtained from the eluate with benzene-ethyl acetate (3:7) and recrystallized from ethyl acetate and n-hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customto give 1.0 g
  6. customThe oily substance was purified by column chromatography (silica gel 20 g.) and 0.6 g

Sources & evidence

ORD record
ord-85d180ccb81f4501a7d653f6e4941035
Source dataset
uspto-grants-1976_01
Patent number
US03935311

Reaction notes

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