Water → HCID 68416730, Verbindung

A solution (15 mL) of methyl 2-chloro-3-(cyanomethyl)benzoate (1.50, 7.16 mmol) produced in Example C61(iii) in dimethylsulfoxide was cooled at which the solution did not solidify, sodium hydride (60%, 869 mg, 21.7 mmol) was slowly added, and the mixture was stirred at room temperature for 30 min. To the suspension was added dropwise 1,3-dibromopropane (1.45 mL, 14.3 mmol), and the mixture was stirred at room temperature for 1.5 hr. To the reaction mixture was slowly added water (50 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with water (50 mL) and saturated brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→50/50) to give the title compound (714 mg, 40%) as a white powder.

1. temperaturewas cooled at which the solution
2. stirringthe mixture was stirred at room temperature for 1.5 hr
3. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
4. washThe organic layer was washed successively with water (50 mL) and saturated brine (50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→50/50)

ORD-Eintrag

ord-766e8d0fa3ba473e9624c0871fac7b8e

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08344135B2