Methyl iodide → 2-Methyl-2-phenyl-cyclopentanone

HRID 1354093

Reaction equation

HRID 1354093 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.IC>C(O)(C)(C)C.O>[CH3:1][C:13]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2901542-PhenylcyclopentanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 3499412-Methyl-2-phenyl-cyclopentanoneYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2-Methyl-2-phenyl-cyclopentanone was prepared using the technique described by Ireland et al., J Org. Chem., 31, 2543 (1966). Potassium tert-butoxide (6.2 g, 55 mmol) was added to a solution of 2-phenylcyclopentanone (8.4 g, 53 mmol) in 100 mL of tert-butanol and the solution was stirred at room temperature for 45 min. Iodomethane (6 mL, 100 mmol) was added and after 2 hours the mixture was diluted with water and extracted twice with ether. The ether extract was washed with water and brine, dried (sodium sulfate) and evaporated. Purification of the residue by flash chromatography (5% ethyl acetate-hexane) afforded 8.3 g of 2-methyl-2-phenyl-cyclopentanone as an oil.

Workup

  1. custom2-Methyl-2-phenyl-cyclopentanone was prepared
  2. extractionextracted twice with ether
  3. extractionThe ether extract
  4. washwas washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customPurification of the residue by flash chromatography (5% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d696319b263a43349f117dfb6fc784da
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Linked notes

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