Reaction #2900

ord-7f93372015354dc38e885820152952ed

Reaction equation

Cc1ncsc1C=O
4-Methyl-5-thiazolecarbaldehyde
CC(C)[O-].CC(C)[O-].CC(C)[O-].[Al+3]
aluminium isopropoxide
[H-].[Na+]
sodium hydride
→
COCc1scnc1C
title compound
COCc1scnc1C
5-Methoxymethyl-4-methylthiazole

Reactants

Cc1ncsc1C=O
4-Methyl-5-thiazolecarbaldehyde
CC(C)[O-].CC(C)[O-].CC(C)[O-].[Al+3]
aluminium isopropoxide
—
alcohol
[H-].[Na+]
sodium hydride

Reagents

None

Solvents

COCCOC
dimethoxyethane
CI
iodomethane
CC(C)O
2-propanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.DISTILLATIONDistillation

Procedure

4-Methyl-5-thiazolecarbaldehyde (J. Amer. Chem. Soc., 1982, 104, 4934-4943) was reduced using aluminium isopropoxide in 2-propanol. The resulting alcohol was treated with sodium hydride in dimethoxyethane and iodomethane was added. Distillation gave the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731335uspto-grants-1998_03