Dimethylformamide → 1,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate

HRID 1429189노트

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HRID 1429189 반응식
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C:8](=[O:10])[CH2:7][C@@H:6]1[C:11]([O:13][CH3:14])=[O:12])=[O:4].C([O-])([O-])=O.[Ca+2].CN(C=O)C>C1COCC1>[CH3:14][O:13][C:11]([CH:6]1[CH2:7][C:8](=[O:10])[CH:9]=[C:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 10112Calcium CarbonateHCID 108996331,2-dimethyl (1R,2S)-4-oxocyclopentane-1,2-dicarboxylate

생성물 1

HCID 591654631,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

(1R,2S)-4-oxo-cyclopentane-1,2-dicarboxylic acid dimethyl ester (4.8 g, 23.8 mmol) and CuBr2 (11.9 g, 53.2 mmol) were dissolved in dry THF (70 ml) and the mixture was refluxed for two hours at 90° C. The formed CuBr was filtrated off and the organic phase was concentrated. CaCO3 (2.7 g, 27.2 mmol) and DMF (70 mL) were added and the mixture was held at 100° C. for one hour. The dark brown mixture was poured over ice (35 g) and the formed precipitate was filtrated off. The aqueous layer was extracted with ethyl acetate (1×300 ml+3×150 ml). The organic phases were dried, filtrated and concentrated. Purification by flash chromatography (toluene/EtOAc 9:1) gave the title compound (2.1 g, 45%) as yellow crystals

후처리

  1. filtrationThe formed CuBr was filtrated off
  2. concentrationthe organic phase was concentrated
  3. filtrationthe formed precipitate was filtrated off
  4. extractionThe aqueous layer was extracted with ethyl acetate (1×300 ml+3×150 ml)
  5. customThe organic phases were dried
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customPurification by flash chromatography (toluene/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-bbb09f1f7b1d466fbb8647a15e939b01
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937080B2

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