Water → 1,3-Cyclopentadiene, octyl-

HRID 323831

Reaction equation

HRID 323831 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Na+].O.C(OCC)C>O1CCCC1>[CH2:2]([C:14]1[CH2:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 81401-BromooctaneHCID 78681Sodium, 2,4-cyclopentadien-1-yl-

Product 1

HCID 5281701,3-Cyclopentadiene, octyl-Yield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a high purity nitrogen atmosphere, 5.8 ml(30mmol) of 1-bromooctane was introduced into a Schlenck flask and 50 ml of tetrahydrofuran (THF) was added thereto. To the resulting mixture, 18 ml of 2N sodium cyclopentadienide in THF was added at 0° C. The resultant was stirred for 5 hours at room temperature, 100 ml of water and 100 ml of diethyl ether were added thereto, followed by agitation. The diethyl ether layer was separated and dried over anhydrous magnesium sulfate. After removing magnesium sulfate, the organic solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: hexane) to obtain 4.21 g of n-octylcyclopentadiene (yield: 79%).

Workup

  1. additionwas added
  2. customThe diethyl ether layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. distillationthe organic solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-8f34f6f247ae44e380591dc60b11e3d8
Source dataset
uspto-grants-2001_04
Patent number
US06214953B1

Linked notes

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