HCID 45084195, compound → 1-(1-Methylcyclopropyl)but-3-en-1-one

Temperature

-60 °C

To a solution of N-methoxy-N,1-dimethylcyclopropanecarboxamide (C50) (18 g, 0.126 mol) in tetrahydrofuran (360 mL) was added a solution of allylmagnesium bromide (1.0 M in diethyl ether, 500 mL, 0.5 mol) drop-wise at −60° C. The mixture was stirred at −60° C. for 1 hour, then was quenched with saturated aqueous ammonium chloride solution (50 mL). The reaction was extracted with dichloromethane (2×500 mL), the organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried, and concentrated in vacuo to give the product as a yellow oil, which was used directly in the next step.

1. customwas quenched with saturated aqueous ammonium chloride solution (50 mL)
2. extractionThe reaction was extracted with dichloromethane (2×500 mL)
3. washthe organic layers were washed with saturated aqueous sodium chloride solution (200 mL)
4. customdried
5. concentrationconcentrated in vacuo

ORD record

ord-d5cb036606494a4d822cb4087777c412

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403846B2