Acetonitrile → HCID 23121212, compound
Reaction equation
C([Li])CCC.CCCCCC.[C:12](#[N:14])[CH3:13].[C:15]1([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[OH:30][CH:29]([C:28]1[CH:31]=[CH:32][C:25]([O:24][CH2:23][CH2:22][CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:26][CH:27]=1)[CH2:13][C:12]#[N:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To dry tetrahydrofuran (14 mL), n-butyl lithium (0.94 mL; a 1.6 M hexane solution) and dry acetonitrile (0.082 mL) were successively dropped at −78° C. After stirring for 30 minutes, a solution of 4-(3-phenylpropoxy)benzaldehyde (300 mg) in dry tetrahydrofuran (3 mL) was dropped into the mixture at −78° C. The reaction mixture was stirred at room temperature for 1 hour, then poured into ice-water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with a mixed solvent of diethyl ether and hexane and filtered to give the title compound (238 mg) having the following physical properties.
Workup
- stirringThe reaction mixture was stirred at room temperature for 1 hour
- extractionextracted with ethyl acetate
- washThe organic layer was successively washed with water
- dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
- concentrationconcentrated
- washThe residue was washed with a mixed solvent of diethyl ether and hexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-eddf86ae16e0433ab25040296302b1fd
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791159B2
Reaction notes
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