Water → HCID 86747077, compound

HRID 1735918Notes

Reaction equation

HRID 1735918 reaction equation
[C:1]1([Li])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.O>C1COCC1>[CH:17]1([C:16]2[CH:15]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:23][CH2:24][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:18][CH2:19][CH:20]=[CH:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 5928226-Methyl-6-phenylfulveneHCID 178506660HCID 178506660, compound

Product 1

HCID 86747077HCID 86747077, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 67.8 mmol of fluorenyllithium in 50 cm3 of THF was added at room temperature to a solution of 11.4 g (67.8 mmol) of 6-methyl-6-phenylfulvene in 40 cm3 of THF. The mixture was stirred at room temperature for 2 hours, and 60 cm3 of water were added. The substance which precipitated was filtered off with suction, washed with diethyl ether and dried in an oil-pump vacuum. 19.1 g (84.2%) of 2,2-cyclopentadienyl(9-fluorenyl)ethylbenzene (correct elemental analyses; 1H-NMR spectrum) were obtained.

Workup

  1. customThe substance which precipitated
  2. filtrationwas filtered off with suction
  3. washwashed with diethyl ether
  4. customdried in an oil-pump vacuum

Sources & evidence

ORD record
ord-44a73ebd1ee54035a16ffca459e6989e
Source dataset
uspto-grants-1996_07
Patent number
US05539066

Reaction notes

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