2-Cyclopenten-1-one → Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

HRID 1289907

반응식

HRID 1289907 반응식
[Br-].[C:2]([CH2:7][S+](C)C)([O:4][CH2:5][CH3:6])=[O:3].N12CCCN=C1CCCCC2.[C:22]1(=[O:27])[CH2:26][CH2:25][CH:24]=[CH:23]1.Cl.[Cl-].[Na+]>C1(C)C=CC=CC=1>[O:27]=[C:22]1[CH2:26][CH2:25][CH:24]2[CH:23]1[CH:7]2[C:2]([O:4][CH2:5][CH3:6])=[O:3]

참가 물질

6

반응물 4

HCID 135882-Cyclopenten-1-oneHCID 78861(2-Ethoxy-2-oxoethyl)dimethylsulphonium bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19796930Hydrochloridesodium chloride

생성물 1

HCID 565357Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate수율 68.3%

시약·촉매·용매 1

HCID 1140Toluene용매

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09c753669ac0443e8dc995dcacdabdd5
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750566

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