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

HRID 2226684ノート

反応式

HRID 2226684 の反応式
N1CCC[C@H]1C(O)=O.[Li]CCCC.[CH3:14][C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.O>CCOCC>[CH:16]1([CH:15]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17]1

参加物

6

反応物 4

HCID 962WaterHCID 145742L-ProlineHCID 5928226-Methyl-6-phenylfulveneHCID 178418339Butyllithium

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 1.4 g. of l-proline (12 mmol) in 40 mL of ether was added 15 mL of n-BuLi (1.6M solution in hexanes, 24 mmol) at 0° C. This solution was stirred overnight at room temperature and then cooled to -78° C. 6-Methyl-6-phenylfulvene, 2.0 g, (12 mmol) in 5 mL of ether was added dropwise at -78° C. The resulting solution was stirred 6 h at -78° C. Water, 20 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 the solvent gave 2.0 g (99% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. D =3.0° (CHCl3), 8.7% ee.

後処理

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

出典と根拠

ORDレコード
ord-6dc8c1949d4e427b9d0222f4d991cc19
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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