Acetic Acid → ALLYL 2-OXOCYCLOPENTANECARBOXYLATE

To a stirring solution of diallyl adipate (4.53 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (40 mL, 1.0 N in THF, 40 mmol). After the addition was complete, the solution was warmed to room temperature and stirred for 2 hours. The reaction mixture was again cooled to 0° C. and the acidified by introducing acetic acid (2.53 mL, 44 mmol) in a dropwise manner. The addition of acetic acid resulted in a turbid mixture which mixture was warmed to room temperature and filtered. The filtrate obtained was concentrated, dissolved in minimal amount of dichloromethane and purified by flash column chromatography (silica gel, dichloromethane) to afford allyl 2-oxocyclopentanecarboxylate (2.62 g, 78%) as a colorless oil. The NMR spectrum for the purified product was the same as that observed for allyl 2-oxocyclopentanecarboxylate prepared using method A.

1. additionAfter the addition
2. temperatureThe reaction mixture was again cooled to 0° C.
3. customresulted in a turbid mixture which mixture
4. temperaturewas warmed to room temperature
5. filtrationfiltered
6. customThe filtrate obtained
7. concentrationwas concentrated
8. dissolutiondissolved in minimal amount of dichloromethane
9. custompurified by flash column chromatography (silica gel, dichloromethane)

ORD record

ord-0085e0216b394ee6b257c9fffccdfec0

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200011B2