ChemicalBook CAS DataBase List 4-METHYL-2-THIAZOLECARBOXALDEHYDE 97

4-METHYL-2-THIAZOLECARBOXALDEHYDE 97 synthesis

8synthesis methods

Product Name:4-METHYL-2-THIAZOLECARBOXALDEHYDE 97
CAS Number:13750-68-0
Molecular formula:C5H5NOS
Molecular Weight:127.16

693-95-8 Synthesis

693-95-8
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13750-68-0
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Yield: 57%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;N-methyl-acetamide;hexane

Steps:

25 4-Methylthiazole-2-carboxaldehyde
Preparation 25 4-Methylthiazole-2-carboxaldehyde A solution of 4-methylthiazole (0.91 mL, 10.0 mmol) in tetrahydrofuran (30 mL) was chilled to -78° C. and butyllithium (6.0 mL, 15 mmol, 2.5 molar solution in hexane) was added dropwise over 15 min. The pale yellow solution was stirred 1 h at -78° C. and became thick slurry. Dimethylformamide (1.2 mL, 15 mmol) was added to the reaction via syringe over 5 min. The reaction was stirred an additional 2 h at -79° C., then allowed to warm at 0° C. and poured onto wet ice. The acidity of the mixture was adjusted to pH 4 with 1 N HCl and extracted with ether. The combined ether extracts were washed with brine, dried over sodium sulfate and concentrated afford 4-methylthiazole-2-carboxaldehyde (0.734 g, 57%) as a brown oil. NMR δ9.88 (s, 1H), 7.29 (s, 1H), 2.50 (s, 3H). The material was used without further purification.

References:

Pfizer Inc. US5962457, 1999, A

693-95-8 Synthesis

693-95-8
336 suppliers
$6.00/5g

4394-85-8 Synthesis