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

HRID 1913592

Reaction equation

HRID 1913592 reaction equation
[CH3:1]C(C)=O.[C:5]([C:9]1[CH2:13][CH:12]=[C:11]([CH3:14])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6].N1CCCC1.C(O[CH2:23][CH3:24])C>CO.O>[C:5]([C:9]1[CH:1]=[C:23]([CH3:24])[C:12](=[C:11]([CH3:10])[CH3:14])[CH:13]=1)([CH3:6])([CH3:7])[CH3:8]

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

In a nitrogen atmosphere, dried acetone (55.2 g, 950.4 mmol) was added dropwise to a solution of 1-tert-butyl-3-methylcyclopentadiene (13.0 g, 95.6 mmol) in dried methanol (130 ml), and subsequently pyrrolidine (68.0 g, 956.1 mmol) was added thereto dropwise. During the dropwise addition, the temperature was kept at 0° C. by ice cooling. The mixture was stirred at room temperature for 4 days. The resultant reaction liquid was diluted with diethyl ether (400 ml), and water (400 ml) was added. The organic phase was separated, then washed with a 0.5 N aqueous hydrochloric acid solution (150 ml×4), water (200 ml×3) and a saturated saline solution (150 ml), and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled away from the filtrate, resulting in a liquid. The liquid was distilled under reduced pressure (70-80° C./0.1 mm Hg) to give 10.5 g of a yellow liquid. The analytical data are given below.

Workup

  1. additionwas added
  2. additionDuring the dropwise addition
  3. customwas kept at 0° C. by ice cooling
  4. customThe resultant reaction liquid
  5. additionwas added
  6. customThe organic phase was separated
  7. washwashed with a 0.5 N aqueous hydrochloric acid solution (150 ml×4), water (200 ml×3)
  8. dry with materiala saturated saline solution (150 ml), and dried over anhydrous magnesium sulfate
  9. filtrationThe desiccant was filtered off
  10. distillationthe solvent was distilled away from the filtrate
  11. customresulting in a liquid
  12. distillationThe liquid was distilled under reduced pressure (70-80° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-c852227507d843fa9b74637e2c184b9e
Source dataset
uspto-grants-2013_12
Patent number
US08609769B2

Linked notes

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