(2-BENZO[1,3]DIOXOL-5-YL-THIAZOL-4-YL)-METHANOL synthesis

5synthesis methods

Product Name:(2-BENZO[1,3]DIOXOL-5-YL-THIAZOL-4-YL)-METHANOL
CAS Number:248249-56-1
Molecular formula:C11H9NO3S
Molecular Weight:235.26

248249-53-8 Synthesis

2-BENZO[1,3]DIOXOL-5-YL-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

248249-53-8
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(2-BENZO[1,3]DIOXOL-5-YL-THIAZOL-4-YL)-METHANOL

248249-56-1
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Yield:248249-56-1 64%

Reaction Conditions:

with dimethylsulfide borane complex in tetrahydrofuran; for 2 h;Heating / reflux;

Steps:

20 Example 20, Synthesis of 2-(benzo[3,4-d]1,3-dioxolan-5-yl)-4-hydroxymethyl-1,3-thiazole(Compound 25)

Ethyl 4-(benzo[3,4-d]1,3-dioxolan-5-yl)-3,5-thiazole carboxylate prepared in Example 17(1.93g, 6.96mmol) was dissolved in tetrahydrofuran(THF, 30mlitre), borane-methylsulfide complex(10M in THF, 2.1mlitre, 20.88mmol) was added thereto, and the mixture was stirred under reflux for 2 hours. The reaction vessel was cooled down to 0°C, and the reaction was stopped by slowly adding 1N-HCl. The pH of the reaction solution was adjusted to 6-7 using saturated sodium bicarbonate solution, and then the organic solvent was removed under reduced pressure. The residue was extracted with ethyl acetate, and then the extract was washed with saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was recrystallized from ethyl acetate and n-hexane(EA/HA=1/1, v/v) to give the title compound(1.04g, Yield 64%) as a white solid. 1H NMR(300 MHz, CDCl3) : δ 2.46(bs, 1H), 4.79(s, 2H), 6.03(s, 2H), 6.88(dd, 1H, J = 3.0, 5.6 Hz), 7.13(s, 1H), 7.48(dd, 1H, J = 1.7, 5.5 Hz)

References:

EP1073428,2004,B1 Location in patent:Page 29