Methanol → 2-(4-Bromo-1-methoxynaphthalen-2-yl-methyl)benzo[b]thiophene
Reaction equation
C([SiH](CC)CC)C.[S:8]1[C:12]([CH:13]([C:15]2[CH:24]=[C:23]([Br:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[O:26][CH3:27])O)=[CH:11][C:10]2[CH:28]=[CH:29][CH:30]=[CH:31][C:9]1=2.CO.O>C(Cl)Cl>[Br:25][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:26][CH3:27])=[C:15]([CH2:13][C:12]2[S:8][C:9]3[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=3[CH:11]=2)[CH:24]=1Participants
Procedure
In a nitrogen stream, triethylsilane (2.48 ml, 15.5 mmol) and a boron trifluoride-diethyl ether complex (1.08 ml, 8.54 mmol) were added dropwise to a solution of benzo[b]thiophen-2-yl-(4-bromo-1-methoxynaphthalen-2-yl)methanol (3.1 g, 7.76 mmol) in methylene chloride (60 ml) at 0° C. and the reaction mixture was stirred at room temperature for two hours, and then a 50% methanol aqueous solution (1 ml) was added and furthermore water (30 ml) was added thereto. The resulting mixture was extracted with methylene chloride, and 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 (1:50)] to obtain the title compound (2.38 g, 80%).
Workup
- extractionThe resulting mixture was extracted with methylene chloride
- 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 (1:50)]
Sources & evidence
- ORD record
- ord-eb65cff3a7e047a2abf5ebc044186c82
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943748B2
Reaction notes
Loading…