Water → 3,5-Dimethyl-4-(hydroxymethyl)isoxazole

To a 0° C. solution of 3,5-dimethyl-1,2-oxazole-4-carbaldehyde (1.0 g, 8.0 mmol) in anhydrous methanol (60 mL) was added sodium borohydride (450 mg, 12.0 mmol). The reaction mixture was stirred at room temperature overnight. Water (50 mL) was added and methanol was evaporated. The resultant mixture was extracted with EtOAc (1×50 mL) and CH2Cl2 (3×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (3,5-dimethyl-1,2-oxazol-4-yl)methanol (805 mg, 79% yield). The product was used without further purification.

1. custommethanol was evaporated
2. extractionThe resultant mixture was extracted with EtOAc (1×50 mL) and CH2Cl2 (3×50 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customdried in vacuo

ORD record

ord-7db866878eec4e9da2e48c3f5a48bff0

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2