Triethylamine → 1-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propene-3-one
Reaction equation
CCCC(O[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])C.[CH:16]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=O.C(N([CH2:33][CH3:34])CC)C>ClCCl.CCCCCC.[Ti](Cl)(Cl)(Cl)Cl>[CH3:25][O:24][C:22]([C:21]1[CH:26]=[CH:27][C:18]([CH:16]=[CH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:9][CH2:8][CH2:10][CH2:11][CH2:33][CH3:34])=[CH:14][CH:15]=2)=[O:9])=[CH:19][CH:20]=1)=[O:23]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of titanium(IV) chloride (11.6 g) in dichloromethane (100 ml) was added 4-n-Pentyloxyacetophenone (10.3 g) and Methyl 4-formylbenzoate (8.21 g) in dichloromethane (50 ml) dropwise at 0° C. To the mixture was added triethylamine (11.15 ml) in dichloromethane (30 ml). The mixture was stirred at 0° C. for 30 minutes and diluted with n-hexane. The organic layer was washed with water (four times), brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with iso-propyl ether. The solid was collected by filtration and dried to give 1-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propen-3-one (4.02 g).
Workup
- washThe organic layer was washed with water (four times), brine
- dry with materialdried over magnesium sulfate
- customThe solvents were removed under reduced pressure
- customthe residue was triturated with iso-propyl ether
- filtrationThe solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-0e034046af04479b927f5267ee72f361
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107458
Reaction notes
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