반응 #1861

반응 방정식

hydrochloric acid sodium chloride

1,8-diazabicyclo[5.4.0]undec-7-ene

carboethoxymethyl dimethylsulfonium bromide

2-cyclopenten-1-one

→

title compound

수율 68.3%

(1SR,5RS,6SR) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate

수율 68.3%

용매

toluene

반응 조건

후처리

1. 1
   workup.WAITAfter an additional 18 hours
2. 2
   추출The resulting mixture was extracted with diethyl ether
3. 3
   건조The combined ether extracts were dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified
7. 7
   세척eluting with a linear gradient of 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

실험 절차

A suspension of carboethoxymethyl dimethylsulfonium bromide (45.5 g) in toluene (350 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (30.2 g). The resulting mixture was stirred at room temperature. After one hour, the reaction mixture was treated with 2-cyclopenten-1-one (19.57 g). After an additional 18 hours, the reaction mixture was added to a 1N 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 of the title compound. Melting point: 36°-38° C.

출처