Isopropyl iodide → 4-(Diethylamino)-2-(1-methylethoxy)benzaldehyde
Reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([OH:12])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:28]([CH3:30])[CH3:29]>CN(C)C=O>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH:28]([CH3:30])[CH3:29])[CH:5]=1)[CH3:14]Participants
Procedure
To a suspension of 4-diethylamino-2-hydroxybenzaldehyde (300 mg, 1.55 mmol), potassium carbonate (428 mg, 3.10 mmol), and cesium carbonate (50 mg, 0.15 mmol) in 1.6 mL of dry N,N-dimethylformamide was added 2-iodopropane (0.47 mL, 4.7 mmol) at room temperature. After being stirred at the same temperature for 7 h, the reaction mixture was filtered to remove inorganic salts. The filtrate was diluted with diethyl ether, and the solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain the title compound as a colorless oil (333 mg, 91%).
Workup
- filtrationthe reaction mixture was filtered
- customto remove inorganic salts
- additionThe filtrate was diluted with diethyl ether
- washthe solution was washed with water, saturated NaHCO3 aqueous solution, brine
- dry with materialdried over MgSO4
- filtrationAfter filtration
- concentrationthe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)
Sources & evidence
- ORD record
- ord-b180625d7c5f447e97dd38125ea53c5f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962674B2
Reaction notes
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