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

HRID 2181374Notes

Reaction equation

HRID 2181374 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-664f7e6dbc4045d5b985f6cdbd068f39
Source dataset
uspto-grants-2005_05
Patent number
US06891005B2

Reaction notes

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