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

HRID 865318ノート

反応式

HRID 865318 の反応式
CC(=O)CCC(=O)C.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.N1CCCC1.CC(OC[C:24]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](COC(C)=O)=[C:30]2C=1C=C[CH:28]=[CH:29]2)=O>CO>[C:10]1(=[C:34]([CH2:35][CH2:36][C:37](=[C:32]2[CH:28]=[CH:29][CH:30]=[CH:31]2)[CH3:24])[CH3:33])[CH:9]=[CH:13][CH:12]=[CH:11]1

参加物

6

反応物 4

HCID 7612CyclopentadieneHCID 80352,5-HexanedioneHCID 31268PyrrolidineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

In a modified reaction procedure [a], 11.0 g (96.3 mmol) of 2,5-hexanedione and 12.7 g (193 mol) 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 aaid 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.

後処理

  1. extraction50 ml of water, and extracted 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

出典と根拠

ORDレコード
ord-203c0b998baa4f2893956ef3aeca67cd
出典データセット
uspto-grants-1996_10
特許番号
US05565534

反応ノート

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