Water → 1,3-Cyclopentadiene, octyl-

HRID 1383696Notes

Reaction equation

HRID 1383696 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 (30 mmol) 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 dried over anhydrous magnesium sulfate. After filtering 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. dry with materialThe diethyl ether layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtering magnesium sulfate
  4. distillationthe organic solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-d425dc7d3c004fe48575805f4eb968c1
Source dataset
uspto-grants-2001_07
Patent number
US06255417B1

Reaction notes

Loading…