3-Methyl-1,2-oxazole-5-carbaldehyde → 1-(3-Methylisoxazol-5-yl)propan-1-ol

Temperature

-78 °C

To a solution of 3-methylisoxazole-5-carbaldehyde (0.801 g, 7.21 mmol) in 10 mL of THF at −78° C. was added ethylmagnesium bromide (3.60 mL, 10.81 mmol) slowly. The reaction mixture was stirred at −78° C. for 2 h, then quenched with saturated aq. NH4Cl solution, and extracted with ether (3×80 mL). The combined organic layers were dried over Na2SO4 filtered and the filtrate was evaporated to provide the crude product. The crude product was purified by chromatography on silica gel, eluting with 10 to 60% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=142.2 (M+1).

1. customquenched with saturated aq. NH4Cl solution
2. extractionextracted with ether (3×80 mL)
3. dry with materialThe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. customthe filtrate was evaporated
6. customto provide the crude product
7. customThe crude product was purified by chromatography on silica gel
8. washeluting with 10 to 60% EtOAc/hexane

ORD record

ord-006e417baad3460e87c1800f85a067a3

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2