Methanol → 6,6-Di(n-butyl)fulvene

HRID 1050650Notes

Reaction equation

HRID 1050650 reaction equation
CO.N1CCCC1.[CH3:8][CH2:9][CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH3:16].[CH:18]1[CH2:22][CH:21]=[CH:20][CH:19]=1>O.C(OCC)C>[CH2:11]([C:12]([CH2:13][CH2:14][CH2:15][CH3:16])=[C:19]1[CH:18]=[CH:22][CH:21]=[CH:20]1)[CH2:10][CH2:9][CH3:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 7612CyclopentadieneHCID 104055-NonanoneHCID 31268Pyrrolidine

Product 1

HCID 190333046,6-Di(n-butyl)fulveneYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, a 200-mL three-necked flask was charged with 15 mL of methanol and 11.8 mL (146 mmol) of pyrrolidine. The mixture was cooled in an ice bath. Subsequently, 20.21 g (144 mmol) of 5-nonanone and 11.0 mL (146 mmol) of cyclopentadiene were added, and the mixture was stirred at room temperature for 22 hours. 100 mL of diethyl ether and 100 mL of water were added to extract the soluble fraction. This organic layer was washed two times with water and once with saturated brine, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography to obtain a target product as a yellow oil (yield 22.53 g (82%)). The target product was identified by 1H-NMR.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionto extract the soluble fraction
  3. washThis organic layer was washed two times with water
  4. dry with materialonce with saturated brine, and dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-09f8dc7b5654498aaa30be268c35192d
Source dataset
uspto-grants-2016_07
Patent number
US09382356B2

Reaction notes

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