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ChemicalBook CAS DataBase List Ethanone, 1-(5-thiazolyl)- (9CI)

Ethanone, 1-(5-thiazolyl)- (9CI) synthesis

4synthesis methods
-

Yield:91516-28-8 90%

Reaction Conditions:

in tetrahydrofuran;diethyl ether at -10 - 20; for 16.16 h;Inert atmosphere;

Steps:

30 [000368j Synthesis of 1-(thiazol-5-yl) ethan-1-one (452):

[000368] Synthesis of 1-(thiazol-5-yl) ethan-1-one (452): To a stirred solution of compound 451 (1.2 g, 6.97 mmol) in THF (20 mL) under argon atmosphere was added methyl magnesium bromide (3.2 mL,10.46 mmol, 3 M solution in Et20) dropwise for 10 mm at -10 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride (30 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through combi flash chromatography using 25-30% EtOAc/ hexanes to afford compound 452 (800 mg, 90%) as white solid. TLC: 50% EtOAc/ hexanes (R 0.6); 1H NMR (DMSO-d6, 400 MHz): ? 9.40 (s, 1H), 8.71 (s, 1H), 2.60 (s, 3H).

References:

WO2015/138895,2015,A1 Location in patent:Paragraph 000368

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