Hexane → HCID 178482589, compound

HRID 1954437Notes

Reaction equation

HRID 1954437 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.[Li]CCCC.[C:22]1([C:28]2[CH:32]=[CH:31][C:30](=[CH2:33])[C:29]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)C=CC=CC=1.[Cl-:40].[Cl-].[Cl-].[Cl-].[Zr+4:44].C[CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>O1CCCC1>[Cl-:40].[Cl-:40].[C:34]1([C:29](=[Zr+2:44]([CH:47]2[CH:48]=[CH:49][CH:50]=[CH:46]2)[C:4]2[C:5]3[CH2:6][C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13]=3[CH:14]=[CH:15][C:3]=2[N:2]([CH3:16])[CH3:1])[C:28]2[CH:22]=[CH:33][CH:30]=[CH:31][CH:32]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 8058Hexane2×HCID 258142-(Dimethylamino)fluoreneHCID 9856075Zirconium chloride (ZrCl4), (T-4)-HCID 22238549Diphenyl FulveneHCID 178418339Butyllithium2×

Product 1

HCID 178482589HCID 178482589, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-78 °C

Procedure

Into a one-liter Schlenk flask were placed 4.26 g of 2-dimethylaminofluorene and 250 mL of tetrahydrofuran. The flask was cooled to -78° C. Into the flask, 11 mL of a 1.72N n-BuLi solution in hexane was gradually added dropwise. The reaction solution was spontaneously brought to room temperature, and then cooled again to -78° C. Thereto, a solution of 5.1 g of diphenylfulvene in 250 mL of tetrahydrofuran was gradually added dropwise. The mixture was stirred vigorously overnight while the temperature thereof was allowed to rise spontaneously to room temperature. A red homogeneous reaction solution was thereby obtained. This reaction solution was washed with a saturated sodium chloride solution, and the solvent was evaporated off. The residue was purified by column chromatography to obtain 7.6 g of slightly yellowish white solid. This solid was placed in another Schlenk flask together with 250 mL of tetrahydrofuran. The mixture was cooled to -78° C. Thereto, 6.5 mL of a 1.72N n-BuLi solution in hexane was gradually added dropwise, and then the mixture was brought to room temperature. To this reaction solution, a solution of 1.15 g of zirconium tetrachloride in 100 mL of tetrahydrofuran was introduced slowly to obtain 1.15 g of intended diphenylmethylene(cyclopentadienyl)(2-dimethylaminofluorenyl)zirconium dichloride. This compound was identified by 1H-NMR as shown in Table 1.

Workup

  1. customwas spontaneously brought to room temperature
  2. temperaturecooled again to -78° C
  3. customto rise spontaneously to room temperature
  4. customA red homogeneous reaction solution was thereby obtained
  5. washThis reaction solution was washed with a saturated sodium chloride solution
  6. customthe solvent was evaporated off
  7. customThe residue was purified by column chromatography
  8. customto obtain 7.6 g of slightly yellowish white solid
  9. temperatureThe mixture was cooled to -78° C
  10. customwas brought to room temperature

Sources & evidence

ORD record
ord-75eb580ceef04648af3b25b9f00fde1a
Source dataset
uspto-grants-2000_09
Patent number
US06121396

Reaction notes

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