Methanol → 2-(4-Bromo-1-methoxynaphthalen-2-yl-methyl)benzo[b]thiophene

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%).

1. extractionThe resulting mixture was extracted with methylene chloride
2. washthe organic layer was washed with a saturated sodium chloride aqueous solution
3. dry with materialdried (anhydrous magnesium sulfate)
4. distillationthe solvent was distilled under reduced pressure
5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:50)]

ORDレコード

ord-eb65cff3a7e047a2abf5ebc044186c82

出典データセット

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07943748B2