Dimethylformamide dimethyl acetal → 2-[(Dimethylamino)methylene]-5,5-dimethylcyclopentanone

HRID 721983

Reaction equation

HRID 721983 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][C:10]1([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]1=[O:15]>>[CH3:6][N:4]([CH:3]=[C:12]1[CH2:13][CH2:14][C:10]([CH3:16])([CH3:9])[C:11]1=[O:15])[CH3:5]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1382862,2-Dimethylcyclopentanone

Product 1

HCID 695835902-[(Dimethylamino)methylene]-5,5-dimethylcyclopentanoneYield 83%

Procedure

A mixture of N,N-dimethylformamide dimethyl acetal (67 mL, 503 mmol) and 2,2-dimethylcyclopentanone (10 g, 90 mmol) was heated at reflux for 2 days. The reaction mixture was then cooled down to room temperature and concentrated. Water (˜380 mL) was added to the residue, and the resulting solution was extracted with methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated to give the title compound (12.5 g) as a yellow-orange oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. concentrationconcentrated
  4. additionWater (˜380 mL) was added to the residue
  5. extractionthe resulting solution was extracted with methylene chloride
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1228a11e329049219729c13590d0d8db
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Linked notes

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