Cyclopentadiene → HCID 15796839, compound

HRID 1699510Notes

Reaction equation

HRID 1699510 reaction equation
Cl[Si:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[CH:28]1([Na])[CH:32]=[CH:31][CH:30]=[CH:29]1.C1CC=CC=1.[H-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.O>[CH:31]1([Si:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:30]=[CH:29][CH:28]=[CH:32]1

Participants

8

Reactant 4

HCID 7612CyclopentadieneHCID 24758Sodium hydrideHCID 27630639-(CHLORODIPHENYLSILYL)-9H-FLUORENEHCID 178507085HCID 178507085, compound

Product 1

HCID 15796839HCID 15796839, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

80 g (0.21 mol) of (2a) were added at 10° C. to an about 2 molar solution of cyclopentadienylsodium in tetrahydrofuran (THF), prepared from 27.8 g (0.42 mol) of freshly cracked cyclopentadiene and 16.7 g (0.42 mol) of 60% strength sodium hydride (as an oil suspension) in 200 ml of THF and the reaction mixture was stirred at room temperature for 3 hours. 300 ml of water and 400 ml of toluene were subsequently added. After phase separation, extraction with a further 250 ml of toluene and drying over magnesium sulfate, the solvents were removed and the residue was taken up in 240 ml of n-heptane. The solid was filtered off, washed with n-heptane and dried under reduced pressure. 57 g (65%) of 2b were obtained.

Workup

  1. customAfter phase separation, extraction with a further 250 ml of toluene
  2. dry with materialdrying over magnesium sulfate
  3. customthe solvents were removed
  4. filtrationThe solid was filtered off
  5. washwashed with n-heptane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-96750350353c41f0b645cda86fa491da
Source dataset
uspto-grants-2002_02
Patent number
US06346635B1

Reaction notes

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