2-Methyl-4-phenylindene → Lithium 2-methyl-4-phenylindenide

HRID 1978169Notes

Reaction equation

HRID 1978169 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=[CH:6][CH:5]=2.[Li:17]CCCC>>[CH3:1][C:2]1[CH-:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=[CH:6][CH:5]=2.[Li+:17]

Participants

3

Reactant 2

HCID 110745592-Methyl-4-phenylindeneHCID 178418339Butyllithium

Product 1

HCID 22023019Lithium 2-methyl-4-phenylindenideYield 89%

Procedure

To a solution of 2-methyl-4-phenylindene (10.03 g, 49.3 mmol) in 200 mL of hexanes was added dropwise over 10 minutes 32 mL of 1.6M n-BuLi. The resulting yellow suspension was stirred for 17 hours. The suspension was filtered and the solid washed twice with 5 mL of hexane. The light yellow solid was dried in vacuo for 2 hours to leave 9.21 g (89 percent yield) of lithium 2-methyl-4-phenylindenide. A second crop (0.61 g) was obtained by concentrating the filtrate to about 80 mL and filtering after 4 hours at room temperature. Overall yield was 9.82 g, 95 percent.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid washed twice with 5 mL of hexane
  3. customThe light yellow solid was dried in vacuo for 2 hours

Sources & evidence

ORD record
ord-d193d01261c84872ba9d007775b441f5
Source dataset
uspto-grants-2001_05
Patent number
US06235917B1

Reaction notes

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