反応 #1148666

反応方程式

2-phenylindene

Butyllithium

2-phenylindene

CH3I

n-butyllithium

→

needles

収率 75.0%

1-Methyl-2-phenylindene

収率 75.0%

溶媒

THF

—

hexanes

反応条件

後処理

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.ADDITIONWhen the addition of the reagents
3. 3
   温度the light brown reaction mixture was heated to 40° C.
4. 4
   workup.STIRRINGstirred for 24 hours
5. 5
   その他After that the solvents were removed in vacuo
6. 6
   その他the light brown solid was recrystallized from EtOH (25 mL) at room temperature

実験手順

Butyllithium (2.5 M in hexanes, 3.0 mL, 7.6 mmol was added dropwise to a suspension of 2-phenylindene (1.382 g, 7.2 mmol) in THF (50 mL) at −78 C. Upon addition of n-butyllithium the reaction mixture turned a dark orange color and 2-phenylindene dissolved. When the addition of the reagents was complete the solution was allowed to warm to room temperature and stirred for 30 minutes. CH3I (1.3 mL, 22 mmol) was added to this solution dropwise and the light brown reaction mixture was heated to 40° C. and stirred for 24 hours. After that the solvents were removed in vacuo and the light brown solid was recrystallized from EtOH (25 mL) at room temperature affording white needles (1.075 g, 75% yield). 1H NMR (CDCl3, 20° C., 300 MHz): δ 7.52-7.19 (overlapping signals from aromatic protons, 9H), 3.74 (s, 2H), 2.31 (s, 3H). 13C {1H}NMR (CDCl3, 20° C., 75 MHz): δ 147.49 (C), 142.42(C), 140.31 (C), 137.56(C), 134.70(C), 128.37 (CH), 128.24 (CH), 126.63 (CH), 126.40 (CH), 124.74 (CH), 123.32 (CH), 119.11 (CH), 40.96 (CH2), 11.94 (CH3).

出典