4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 18936369, compound

HRID 2832

Reaction equation

HRID 2832 reaction equation
C([Li])CCC.[OH:6][CH2:7][CH2:8][C:9]1[S:13][CH:12]=[N:11][C:10]=1[CH3:14].[C:15]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)(=[O:17])[CH3:16]>O1CCCC1>[OH:6][CH2:7][CH2:8][C:9]1[S:13][C:12]([C:15]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)([OH:17])[CH3:16])=[N:11][C:10]=1[CH3:14]

Participants

5

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 151161-(Thiophen-3-yl)ethanoneHCID 178418339Butyllithium

Product 1

HCID 18936369HCID 18936369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexanes, 75 mmoles) was added to a stirred solution of 5-(2-hydroxyethyl)-4-methylthiazole (35 mmoles) in dry tetrahydrofuran (80 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 3-acetylthiophene (38 mmoles) in dry tetrahydrofuran (10 ml) was added dropwise. After 1 hour the mixture was allowed to warm to room temperature and was then stirred overnight. The normal work-up followed by column chromatography then gave the title compound.

Workup

  1. waitAfter 1 hour the mixture was allowed

Sources & evidence

ORD record
ord-5a5eb6ad04954fd4aa68e9d330119b48
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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