Acetone → 1,6,6-Trimethyl-3-tert-butyl-fulvene

HRID 270983Notes

Reaction equation

HRID 270983 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[C:7]([CH3:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:11]C(C)=O.N1CCCC1.C(O[CH2:23][CH3:24])C>CO.O>[C:1]([C:5]1[CH:11]=[C:23]([CH3:24])[C:8](=[C:7]([CH3:6])[CH3:10])[CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 31268PyrrolidineHCID 153198441-Tert-butyl-3-methylcyclopenta-1,3-diene

Product 1

HCID 27627611,6,6-Trimethyl-3-tert-butyl-fulvene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 13.0 g (95.6 mmol) of 1-tert-butyl-3-methylcyclopentadiene in 130 ml of dehydrated methanol, 55.2 g (950.4 mmol) of dehydrated acetone was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, and 68.0 g (956.1 mmol) of pyrrolidine was further dropwise added, followed by stirring at room temperature for 4 days. After the reaction solution was diluted with 400 ml of diethyl ether, 400 ml of water was added. The organic phase was separated, washed with a 0.5N hydrochloric acid aqueous solution (150 ml×4), water (200 ml×3) and a saturated saline solution (150 ml), and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (70-80° C./0.1 mmHg) to obtain 10.5 g of a yellow liquid. The analyzed values are given below.

Workup

  1. additionwas further dropwise added
  2. additionwas added
  3. customThe organic phase was separated
  4. washwashed with a 0.5N hydrochloric acid aqueous solution (150 ml×4), water (200 ml×3)
  5. dry with materiala saturated saline solution (150 ml), and then dried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered
  7. distillationfrom the filtrate the solvent was distilled off
  8. customto obtain a liquid
  9. distillationThe liquid was subjected to vacuum distillation (70-80° C./0.1 mmHg)

Sources & evidence

ORD record
ord-db3bd2deca0d4e5aab3042aaaca14277
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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