Hydrochloric Acid → HCID 23503257, compound

Temperature

-78 °C

3-Furoic acid (2.85 g) was dissolved in tetrahydrofuran (50 ml) and cooled to −78° C. A solution of lithium diisopropylamide (56 mmol) in tetrahydrofuran (100 ml) was added dropwise and the mixture was stirred for 15 minutes. A solution of 3-methylbutanal (3.0 ml) in tetrahydrofuran (15 ml) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h and then allowed to warm to ambient temperature. The mixture was poured into water, the aqueous phase was acidified with 2M hydrochloric acid and the mixture was extracted twice with ethyl acetate. The organic phases were washed with brine, dried, filtered and evaporated. Chromatography, eluting with dichloromethane:ethyl acetate:acetic acid (160:40:1), gave the sub-title compound (2.75 g).

1. stirringThe reaction mixture was stirred at −78° C. for 1 h
2. temperatureto warm to ambient temperature
3. extractionthe mixture was extracted twice with ethyl acetate
4. washThe organic phases were washed with brine
5. customdried
6. filtrationfiltered
7. customevaporated
8. washChromatography, eluting with dichloromethane:ethyl acetate:acetic acid (160:40:1)

ORD record

ord-498134f42d1d4d81aa7db0bfabb9ffbe

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06770646B2