Water → [1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene

HRID 2226688ノート

反応式

HRID 2226688 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.O>CCOCC.CCCCCC>[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

7

反応物 4

HCID 962WaterHCID 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 79%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

To a solution of 0.77 mL 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 hexanes, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. The solvent was removed under vacuum and 25 mL of hexane added. 6-Methyl-6-phenylfulvene, 1.06 (6 mmol) in 5 mL of hexane was added dropwise at -78° C. The resulting yellow solution was stirred for 7 h at -78° C. Water, 25 mL, was added dropwise 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 0.8 g (79% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. [α]D =2.0 ° (CHCl3), 5.8% ee.

後処理

  1. customThe solvent was removed under vacuum and 25 mL of hexane
  2. additionadded
  3. stirringThe resulting yellow solution was stirred for 7 h at -78° C
  4. temperaturethe solution warmed to room temperature
  5. customThe organic layer was separated
  6. washwashed with aqueous NaHCO3, H2O
  7. dry with materialdried over MgSO4
  8. customRemoval of solvent

出典と根拠

ORDレコード
ord-23a2915ad1494c7286fe8a7ae6bea9be
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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