2-Cyclopenten-1-one → ethyl (1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylate

A suspension of carboethoxymethyl dimethylsulfonium bromide (45.5 g, 198.6 mmol) in toluene (350mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (30.2 g, 198.4 mmol). The resulting mixture was stirred at room temperature. After one hour, the reaction mixture was treated with 2-cyclopenten-1-one (19.57 g, 238.4 mmol). After an additional 18 hours, the reaction mixture was added to a 1 N hydrochloric acid/sodium chloride solution. The resulting mixture was extracted with diethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica-gel chromatography, eluting with a linear gradient of 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes, to give 22.81 g (68%) of the title compound. Melting point: 36-38° C.

1. waitAfter an additional 18 hours
2. extractionThe resulting mixture was extracted with diethyl ether
3. dry with materialThe combined ether extracts were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified
7. washeluting with a linear gradient of 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

ORD-Eintrag

ord-a99dddab673340a385d556171f8ffed8

Quelldatensatz

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06160009