Cyclopentene → Ethyl 3-cyclopenten-1-ylbenzoate

HRID 1767759노트

반응식

HRID 1767759 반응식
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13]1[CH2:17][CH2:16][CH2:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C(O)C>[C:13]1([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:17][CH2:16][CH2:15][CH:14]=1

참가 물질

6

반응물 3

HCID 8882CyclopenteneHCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoate

생성물 1

HCID 12094926Ethyl 3-cyclopenten-1-ylbenzoate

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

The following are successively introduced into a round-bottomed flask: 7 g of ethyl 3-iodobenzoate (25 mmol), 11.2 ml of cyclopentene (127 mmol), 21 ml of ethanol, 1.16 g of Pd2dba3 complex (1.27 mmol), 8.8 g of potassium carbonate (63 mmol) and 8.17 g of nBu4NBr (25 mmol). The medium is heated at 80° C. for 16 hours and then the black mixture is filtered on celite. The precipitate is washed with ethyl acetate. The filtrate is washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The title product, which is isolated by bulb to bulb distillation (5.2 g), is obtained in the form of a pale yellow oil.

후처리

  1. additionThe following are successively introduced into a round-bottomed flask
  2. filtrationthe black mixture is filtered on celite
  3. washThe precipitate is washed with ethyl acetate
  4. washThe filtrate is washed with water
  5. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1390fa391864490eb5ecd8fae029f29d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235568B2

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