تفاعل #1148666

معادلة التفاعل

2-phenylindene

Butyllithium

2-phenylindene

CH3I

n-butyllithium

→

needles

المردود 75.0%

1-Methyl-2-phenylindene

المردود 75.0%

المذيبات

THF

—

hexanes

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر