Dichloromethane → HCID 178423640, compound

HRID 413499Notes

Reaction equation

HRID 413499 reaction equation
[Li+].[CH3:2][CH2:3][CH2:4][CH2-:5].[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[Cl-:15].[Cl-].[Cl-].[Cl-].[Zr+4:19].C(Cl)[Cl:21]>CCOCC>[Cl-:21].[Cl-:15].[CH3:2][C:3]1[CH:14]=[CH:6][C:7]([C:7]2[CH:8]([Zr+2:19][CH:6]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[C:7]3[C:3]3[CH:2]=[CH:8][C:9]([CH3:10])=[CH:5][CH:4]=3)[C:9]3[C:14]([CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7219IndeneHCID 61028n-Butyl lithiumHCID 9856075Zirconium chloride (ZrCl4), (T-4)-

Product 1

HCID 178423640HCID 178423640, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Butyllithium (1.6 M in hexanes, 4.2 mL, 6.7 mmol) was added dropwise to a solution of 2-(4-methyl)phenyl)indene (1.323 g, 6.4 mmol) in Et2O (20 mL). The red-orange solution was stirred at ambient temperature for 30 min after which time the solvent was removed in vacuo. In a drybox, to the resulting solid was added ZrCl4 (0.754 g, 3.2 mmol). The solids were cooled to −78° C. and methylene chloride (60 mL) was slowly added. The solution was warmed to room temperature and kept there overnight. The resulting yellow-orange turbid solution was then filtered over a plug of Celite and the Celite was washed with CH2Cl2 until the washings were colorless (ca. 60 mL). The product was recrystallized from CH2Cl2/hexane at −18° C. Yield: 577 mg (31%). 1H NMR (C6D6, 23°C., 400 MHz): d7.36 (d, J=8 Hz, 4H); 7.11 (m, 4H); 7.02 (d, J=8 Hz, 4H); 6.92 (m, 4H); 6.43 (s, 4H, Cp-H); 2.17 (s, 6H, CH3). C, H analysis (crystallizes with 1/2 CH2Cl2): Anal. Found (Calcd.): C, 63.21 (63.46); H, 4.41 (4.42).

Workup

  1. customwas removed in vacuo
  2. temperatureThe solids were cooled to −78° C.
  3. temperatureThe solution was warmed to room temperature
  4. waitkept there overnight
  5. filtrationThe resulting yellow-orange turbid solution was then filtered over a plug of Celite
  6. washthe Celite was washed with CH2Cl2 until the washings
  7. customThe product was recrystallized from CH2Cl2/hexane at −18° C
  8. customC, H analysis (crystallizes with 1/2 CH2Cl2)

Sources & evidence

ORD record
ord-fbbef01a86df4fa183a8ed863704564a
Source dataset
uspto-grants-2003_05
Patent number
US06566544B1

Reaction notes

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