Cyclopropyl methyl ketone → HCID 23237111, compound

Temperature

-78 °C

Hexamethyldisilazane (1 g, 6.2 mmol) and diethylether were taken in RBF and cooled to −78° C. under nitrogen atmosphere. n-BuLi (7.7 ml) was added and stirred for 15 mins Cyclopropyl methyl ketone (0.66 ml, 6.8 mmol) was added and stirred at −78° C. for 45 mins. At this stage methyl 2,2-difluoroacetate (1.62 ml, 18.58 mmol) was added and brought the reaction mixture to rt and allowed to stir for overnight. Reaction mixture quenched with water, ether layer separated and aqueous layer was acidified with 1N HCl. Aqueous layer extracted with diethyl ether and ether was dried over anhydrous Na2SO4. Diethyl ether was removed on rotavapour to obtain the title compound (390 mg) which was used in the next step without further purification. 1H-NMR (δ ppm, CDCl3, 400 MHz): 6.08 (s, 1H), 5.95 (t, J 54.2, 1H), 1.84-1.76 (m, 1H), 1.34-1.29 (m, 2H), 1.10-1.03 (m, 2H).

1. additionwas added
2. customto rt
3. stirringto stir for overnight
4. customReaction mixture
5. customquenched with water, ether layer
6. customseparated
7. extractionAqueous layer extracted with diethyl ether and ether
8. dry with materialwas dried over anhydrous Na2SO4
9. customDiethyl ether was removed on rotavapour

ORD record

ord-d7dcd233eac14bd1be656cc9a0fd25d7

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377970B2