Methyl iodide → 1-methyl-2-phenylindene

HRID 411812Notes

Reaction equation

HRID 411812 reaction equation
[CH2:1]([Li])CCC.[C:6]1([C:12]2[CH2:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CI>C1COCC1>[CH3:1][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[C:12]1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3534352-Phenyl-1H-indene2×HCID 178418339Butyllithium2×

Product 1

HCID 27530641-methyl-2-phenylindeneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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): Λ 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□1147.49 (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).

Workup

  1. dissolutiondissolved
  2. additionWhen the addition of the reagents
  3. temperaturethe light brown reaction mixture was heated to 40° C.
  4. stirringstirred for 24 hours
  5. customAfter that the solvents were removed in vacuo
  6. customthe light brown solid was recrystallized from EtOH (25 mL) at room temperature

Sources & evidence

ORD record
ord-31b698163834482785225e8dd7370f94
Source dataset
uspto-grants-2003_05
Patent number
US06559262B1

Reaction notes

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