Dimethylformamide dimethyl acetal → 2-[(Dimethylamino)methylene]-5,5-dimethylcyclopentanone
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
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
- temperaturewas heated
- temperatureat reflux for 2 days
- concentrationconcentrated
- additionWater (˜380 mL) was added to the residue
- extractionthe resulting solution was extracted with methylene chloride
- customThe organic layer was separated
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1228a11e329049219729c13590d0d8db
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138361B2
Reaction notes
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