Reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=1[CH:11]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
In a nitrogen stream, to a solution of 2-benzyloxy-5-methoxy-benzaldehyde (2.0 g, 8.25 mmol) in THF (50 mL), a solution of 4-methoxyphenylmagnesium bromide in THF (0.5 M, 19.8 mL) was added dropwise under cooling with ice. The mixture solution was stirred at room temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto under cooling with ice and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:1)] to obtain the title compound (2.9 g, 100%).
Workup
- temperatureunder cooling with ice
- temperatureunder cooling with ice
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with a saturated sodium chloride aqueous solution
- dry with materialdried (anhydrous magnesium sulfate)
- distillationthe solvent was distilled under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:1)]
Sources & evidence
- ORD record
- ord-30ecc1095d294396a8903d057ee68626
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048897B2
Linked notes
Loading…