Hydrochloric Acid → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[N:7][CH:8]=1.[C:13]1(N2CCOCC2)[CH2:17][CH2:16][CH2:15][CH:14]=1.Cl.C(=O)(O)[O-:26].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[C:14]2[CH2:15][CH2:16][CH2:17][C:13]2=[O:26])=[N:7][CH:8]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-(trifluoromethyl)pyridine-2-carbaldehyde (3.32 g, 18.96 mmol) and 4-(cyclopent-1-en-1-yl)morpholine (CAS number 936-52-7; 2.97 ml, 18.58 mmol) in toluene (50 ml) was heated to 90° C. for 18 hours. The reaction was then cooled to room temperature and concentrated HCl (2 ml) and water (2 ml) was added drop wise. The reaction was stirred at room temperature for 20 minutes and then neutralised with a saturated solution of sodium bicarbonate and then basified with 2M NaOH (aq). The organics were extracted with ethyl acetate (2×40 ml) and the combined organics were washed with brine (10 ml), dried over magnesium sulfate, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound.
Workup
- extractionThe organics were extracted with ethyl acetate (2×40 ml)
- washthe combined organics were washed with brine (10 ml)
- dry with materialdried over magnesium sulfate
- filtrationfiltered through a hydrophobic frit
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol)
Sources & evidence
- ORD record
- ord-d716829f9577459c95d630faea0d20e8
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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