Tetrahydrofuran → ethyl 4-(hydroxymethyl)thiazole-2-carboxylate

HRID 2203098Notes

Reaction equation

HRID 2203098 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11](O)=[O:12])[N:10]=1)=[O:5])[CH3:2].C1COCC1>CO>[OH:12][CH2:11][C:9]1[N:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][CH:8]=1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 534878632-(Ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid

Product 1

HCID 43558808ethyl 4-(hydroxymethyl)thiazole-2-carboxylateYield 51.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid (2 g), boran-THF complex (1.0 M in THF, 45.2 ml) and THF (50 ml) was heated under reflux overnight. After MeOH (2.0 ml) was added to the mixture at the same temperature, the mixture was concentrated in vacuo to dryness. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (0.96 g) as a white solid.

Workup

  1. temperatureunder reflux overnight
  2. concentrationthe mixture was concentrated in vacuo to dryness
  3. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-e496314232ef4df18834c018eb66ffb8
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…