Cyclopentene → Ethyl 3-cyclopenten-1-ylbenzoate

HRID 1373987ノート

反応式

HRID 1373987 の反応式
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

参加物

6

反応物 3

HCID 8882CyclopenteneHCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoate

生成物 1

HCID 12094926Ethyl 3-cyclopenten-1-ylbenzoate

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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 Pd2 dba3 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.

後処理

  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

出典と根拠

ORDレコード
ord-49045b4c34f04fb9bac4eafebdc6e208
出典データセット
uspto-grants-2007_01
特許番号
US07163957B2

反応ノート

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