Acetic Acid → 5,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

HRID 726834노트

반응식

HRID 726834 반응식
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.N1[CH2:18][CH2:17][CH2:16][CH2:15]1.[C:19](O)(=O)C>CO.O>[C:10]1(=[C:2]([CH2:3][CH2:4][C:5](=[C:6]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH3:19])[CH3:1])[CH:9]=[CH:13][CH:12]=[CH:11]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7612CyclopentadieneHCID 80352,5-HexanedioneHCID 31268Pyrrolidine

생성물 1

HCID 149519975,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

In a modified reaction procedure [a], 11.0 g (96.3 mmol) of 2,5-hexanedione and 12.7 g (193 mmol) of freshly cracked cyclopentadiene are dissolved in 60 ml of methanol, the solution is cooled to 0° C., and 8.60 g (121 mmol) of pyrrolidine are added. The reaction solution is stirred at 0° C. for 90 minutes, hydrolyzed using 5 ml of glacial acetic acid and 50 ml of water, and extracted twice with 70 ml of diethyl ether in each case, and the combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, giving, after removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue.

후처리

  1. extractionextracted twice with 70 ml of diethyl ether in each case
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customgiving
  5. customafter removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue

출처 및 근거

ORD 기록
ord-06b1d13fa96741a394e6f958ea2a4e97
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710297

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