Acetone → 3-(1,1-Dimethylpropyl)-6,6-dimethylfulvene

HRID 270996Notes

Reaction equation

HRID 270996 reaction equation
[CH3:1][C:2]([C:6]1[CH2:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[CH3:11][C:12]([CH3:14])=O.N1CCCC1>CO.CCOCC.O>[CH3:1][C:2]([C:6]1[CH:10]=[CH:9][C:8](=[C:12]([CH3:14])[CH3:11])[CH:7]=1)([CH3:5])[CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 12779334(1,1-Dimethylpropyl)cyclopentadiene

Product 1

HCID 178181473-(1,1-Dimethylpropyl)-6,6-dimethylfulveneYield 48%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution-of 3.00 g (22.0 mmol) of (1,1-dimethylpropyl)cyclopentadiene in 30 ml of methanol, 16.2 ml (220.4 mmol) of acetone and 3.7 ml (44.0 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (100° C./1 mmHg) to obtain 1.85 g (10.49 mmol) of a yellow liquid (yield: 48%). The analyzed values are given below.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materiala saturated saline solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. distillationThe liquid was subjected to vacuum distillation (100° C./1 mmHg)

Sources & evidence

ORD record
ord-bb55cb5f99fe458b9d187e37c32817ec
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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