Water → Ethyl 3-cyclopropyl-3-oxopropanoate

Temperature

-65 °C

To a cooled (-70° C.) solution of monoethyl malonate (33.97 g, 257.10 mmol) in THF (639 mL) was added n-BuLi (1.6M in hexanes, 319 mL, 514.19 mmol) and the mixture was stirred under an argon atmosphere for 15 min. The resulting solution was cooled to -65° C. and cyclopropanecarbonyl chloride (15.55 g, 148.77 mmol) was added. The reaction mixture was stirred for 1 h and then allowed to warm up to room temperature. Some drops of water were added and THF was removed. The residue was taken up in 1N HCl/Et2O and extracted with Et2O. The organic phase was washed with saturated NaHCO3, dried and concentrated to a residue. This was purified by chromatography on silica gel (hexane-EtOAc mixtures of increasing polarity) to afford the title compound as a yellow oil (14.7 g, 63%).

1. stirringThe reaction mixture was stirred for 1 h
2. temperatureto warm up to room temperature
3. customTHF was removed
4. extractionextracted with Et2O
5. washThe organic phase was washed with saturated NaHCO3
6. customdried
7. concentrationconcentrated to a residue
8. customThis was purified by chromatography on silica gel (hexane-EtOAc mixtures of increasing polarity)

ORD record

ord-117880648df945d9b2ebf40b25cde8c4

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05827863