1H-Indene, 2-(1-methylethyl)-4-phenyl- → Lithium 2-isopropyl-4-phenylindenide

HRID 1595108Notes

Reaction equation

HRID 1595108 reaction equation
[CH:1]([C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].C([Li:23])CCC>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH-:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].[Li+:23]

Participants

4

Reactant 2

HCID 180082381H-Indene, 2-(1-methylethyl)-4-phenyl-HCID 178418339Butyllithium

Product 1

HCID 22023052Lithium 2-isopropyl-4-phenylindenideYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene solution (25 ml) of 2-isopropyl-4-phenylindene (3.34 g, 14.25 mmol), in a glovebox filled with argon, was added n-butyl lithium (5.500 ml, 13.75 mmol). The mixture was stirred at room temperature overnight. The toluene was removed under reduced pressure. Hexane (20 ml) was added and removed under reduced pressure then added again (50 ml). The mixture was stirred for 1 h then filtered, washed with about 15 ml hexane and the filtrate dried under vacuum. The lithium indenide product (3.09 g) was obtained as an orange-brown powder. This material was stored in the glovebox until needed.

Workup

  1. customThe toluene was removed under reduced pressure
  2. additionHexane (20 ml) was added
  3. customremoved under reduced pressure
  4. additionthen added again (50 ml)
  5. stirringThe mixture was stirred for 1 h
  6. filtrationthen filtered
  7. washwashed with about 15 ml hexane
  8. customthe filtrate dried under vacuum

Sources & evidence

ORD record
ord-0b5fdc7fdcb94c1e9053fdd10e30b0e2
Source dataset
uspto-grants-2001_09
Patent number
US06284905B1

Reaction notes

Loading…