Reaction equation
Br[Zn][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:9]([C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])=[CH:10][CH3:11].Cl.C(OCC)(=O)C>C1COCC1>[OH:13][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH:9]=[CH:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Procedure
Under nitrogen atmosphere, 15 mL of THF was added to 3.05 g (5 mmol, 1.0 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 0.73 g (5 mmol) of phenyl propenyl ketone in 2.5 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 3 hours. 7.5 mL of 1N hydrochloric acid was added at 20° C. or lower, followed by dilution with 25 mL of ethyl acetate. Then, the layers were separated. The organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 10 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution. After washing, the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3) afforded 1.09 g of the desired product (yield 93%).
Workup
- stirringThe mixture was stirred at 20˜25° C. for 3 hours
- customThen, the layers were separated
- washThe organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 10 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution
- washAfter washing
- dry with materialthe organic layer was dried with anhydrous magnesium sulfate
- concentrationAfter concentration
- customunder reduced pressure, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3)
Sources & evidence
- ORD record
- ord-4f9bc8246761468f9999bb03cc64cfd6
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093403B2
Linked notes
Loading…