6-Methyl-6-phenylfulvene → [1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene

HRID 2226685ノート

反応式

HRID 2226685 の反応式
[Li][C@H]1CC(C(O)=O)N([Li])C1=O.[Li]CCCC.[CH3:17][C:18]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1>CCOCC>[CH:19]1([CH:18]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20]1

参加物

5

反応物 3

HCID 5928226-Methyl-6-phenylfulveneHCID 178418339ButyllithiumHCID 178506840HCID 178506840、化合物

生成物 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene収率 99%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 0.77 g of dilithio (s)-(-)-2-pyrrolidone-5-carboxylic acid (6 mmol) in 40 mL of ether was added 7.8 mL of n-BuLi (1.6M solution in hexances, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. 6-Methyl-6-phenylfulvene, 1.0 g, (6 mmol) in 5 mL of ether was added dropwise at -78° C. and the color of the reaction mixture turned green. The resulting solution was stirred for 7 h at -78° C. and the solution warmed to room temperature. The organic layer was separated and washed with aqueous NaHCO3, H2O and then dried over MgSO4. Removal of solvent gave 1.0 g (99% yield) of 1-cyclopentadienyl-1-phenyl-ethane as a light yellow oil. [α]D =6.0° (CHCl3), 17.4% ee.

後処理

  1. stirringThe resulting solution was stirred for 7 h at -78° C.
  2. temperaturethe solution warmed to room temperature
  3. customThe organic layer was separated
  4. washwashed with aqueous NaHCO3, H2O
  5. dry with materialdried over MgSO4
  6. customRemoval of solvent

出典と根拠

ORDレコード
ord-69bfc291c1b24ea186012bd2aa8cc485
出典データセット
uspto-grants-1994_09
特許番号
US05349100

反応ノート

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