Ethyl Acetate → 2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH:14]1([CH2:17][NH:18][CH2:19][CH2:20][CH3:21])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[CH:14]1([CH2:17][N:18]([CH2:19][CH2:20][CH3:21])[C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:16][CH2:15]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
2-Fluoro-5-trifluoromethyl-benzaldehyde (1.3 g) and cyclopropylmethyl-propyl-amine (1.15 g) are dissolved in toluene (13 ml), and thereto is added potassium carbonate (2.81 g) and the mixture is stirred at 120° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→97:3) to give 2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde (1.7 g). MS (m/z): 286 [M+H]+
Workup
- temperatureThe reaction solution is cooled to room temperature
- customthe mixture is separated
- washthe organic layer is washed with a saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→97:3)
Sources & evidence
- ORD record
- ord-04a5abb2096c4251aa38342541870e2d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906517B2
Reaction notes
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