Aluminium lithium hydride → (4-Ethylthiazol-5-yl)methanol

Temperature

0 °C

To a 0° C. mixture of lithium aluminum hydride (800 mg, 21.0 mmol) in anhydrous THF (30 mL) was slowly added a solution of ethyl 4-ethyl-1,3-thiazole-5-carboxylate (1.91 g, 10.3 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was quenched with 5 N NaOH. Water (150 mL) and EtOAc (150 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (1×100 mL). The combined organic extracts were back extracted with brine (2×200 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (4-ethyl-1,3-thiazol-5-yl)methanol (1.05 g, 71% yield). The product was used without further purification.

1. customThe reaction was quenched with 5 N NaOH
2. additionWater (150 mL) and EtOAc (150 mL) were added
3. stirringThe mixture was stirred for 30 minutes
4. customThe solid material was removed by filtration
5. customThe organic layer was recovered
6. extractionThe aqueous layer was extracted with EtOAc (1×100 mL)
7. extractionThe combined organic extracts were back extracted with brine (2×200 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated
11. customdried in vacuo

ORD record

ord-7370bb80b4e64f5ca1bcc5f72febcfde

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2