Acetone → 2-Butyl-6,6-dimethylfulvene

HRID 1275866Notes

Reaction equation

HRID 1275866 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])C.CC(C)=O.N1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH2:15]([C:8]1[CH:7]=[CH:6][C:5](=[C:1]([CH3:3])[CH3:4])[CH:9]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 633714Tert-butylcyclopentadiene

Product 1

HCID 178963752-Butyl-6,6-dimethylfulveneYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of t-butylcyclopentadiene (15 g, 123 mmol), acetone (9.0 mL, 135.2 mmol), pyrrolidine (11.7 mL, 135.3 mmol) and methanol (100 mL) was stirred at 0° C., for 30 minutes, and then at room temperature overnight. The reaction mixture was quenched with acetic acid (7.38 g) and with water (100 mL) at 0° C. The mixture was extracted with Et2O (3×200 mL); the organic layers were combined, washed with a saturated solution of NaHCO3, dried over anhydrous magnesium sulphate, filtered and finally concentrated, thus yielding 2-butyl-6,6-dimethylfulvene in the form of a yellow liquid (18.24 g, 92% yield).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture was quenched with acetic acid (7.38 g) and with water (100 mL) at 0° C
  4. extractionThe mixture was extracted with Et2O (3×200 mL)
  5. washwashed with a saturated solution of NaHCO3
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationfinally concentrated

Sources & evidence

ORD record
ord-17096a16e3fa42ea8470d07a22a0de7e
Source dataset
uspto-grants-2000_12
Patent number
US06162937

Reaction notes

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