Acetone → HCID 22327789, compound

HRID 271010Notes

Reaction equation

HRID 271010 reaction equation
[CH3:1][C:2]([C:7]1[CH2:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[CH2:3][CH2:4][CH3:5].[CH3:12][C:13]([CH3:15])=O.N1CCCC1>CO.CCOCC.O>[CH3:6][C:2]([C:7]1[CH:11]=[CH:10][C:9](=[C:13]([CH3:15])[CH3:12])[CH:8]=1)([CH3:1])[CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 12779343HCID 12779343, compound

Product 1

HCID 22327789HCID 22327789, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.00 g (20.0 mmol) of (1,1-dimethylbutyl)cyclopentadiene in 30 ml of methanol, 14.6 ml (198.8 mmol) of acetone and 2.5 ml (29.9 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for 3 days. 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 isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.70 g (14.19 mmol) of a yellow liquid (yield: 71%). 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. customThe liquid was isolated
  9. custompurified by column chromatography (silica gel, developing solvent: hexane)

Sources & evidence

ORD record
ord-f39bd23e8c9141d2bbca7361a13ba297
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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