Aluminium lithium hydride → HCID 59589390, compound

Temperature

0 °C

To a 0° C. mixture of LAH (270 mg, 7.1 mmol) in anhydrous THF (10 mL) was slowly added a solution of ethyl 3,5-diethyl-1,2-oxazole-4-carboxylate (826 mg, 4.7 mmol) in anhydrous THF (10 mL). The mixture was stirred at 0° C. for 5 hours, and the mixture was then quenched with 5 N NaOH. Water (50 mL) and EtOAc (50 mL) were added. The mixture was stirred for 30 minutes. The solids were filtered, and the organic layer was recovered. The aqueous layer was extracted with EtOAc (1×50 mL). The combined organic extracts were washed with brine (1×200 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (3,5-diethyl-1,2-oxazol-4-yl)methanol (710 mg, 97% yield), which was used without further purification.

1. customthe mixture was then quenched with 5 N NaOH
2. additionWater (50 mL) and EtOAc (50 mL) were added
3. stirringThe mixture was stirred for 30 minutes
4. filtrationThe solids were filtered
5. customthe organic layer was recovered
6. extractionThe aqueous layer was extracted with EtOAc (1×50 mL)
7. washThe combined organic extracts were washed with brine (1×200 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated
11. customdried in vacuo

ORD record

ord-3cfca96aadd14b2b85a810dd3c56ffc3

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315521B2