Methyl 2,1,3-benzothiadiazole-5-carboxylate → 2,1,3-Benzothiadiazol-5-ylmethanol

Temperatur

0 °C

To a suspension of lithium aluminum hydride (215 mg, 5.7 mmol) in diethyl ether (15 mL) at 0° C. was added methyl 2,1,3-benzothiadiazole-5-carboxylate (1.0 g, 5.2 mmol) in one portion. The reaction mixture was allowed to stir at 0° C. for 10 min, then at room temperature for 24 h. Ethyl acetate (30 mL) was added very slowly dropwise at 0° C. The reaction mixture was then added slowly to an aqueous solution of potassium sodium tartrate (30% w/v; 100 mL) and stirred for 2 h. The reaction mixture was diluted with 100 mL of ethyl acetate and the layers were separated. The aqueous layer was re-extracted with ethyl acetate (1×100 mL). The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel, 25% ethyl acetate in petroleum ether) to give 2,1,3-benzothiadiazole-5-methanol (400 mg, 47% yield) as an orange solid.

1. waitat room temperature for 24 h
2. stirringstirred for 2 h
3. customthe layers were separated
4. extractionThe aqueous layer was re-extracted with ethyl acetate (1×100 mL)
5. dry with materialThe combined organic layers were dried (MgSO4)
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe crude product was purified by flash chromatography (silica gel, 25% ethyl acetate in petroleum ether)

ORD-Eintrag

ord-4e1c73c88041466d89710302cc2cab3b

Quelldatensatz

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06515124B2