Diisopropylamine → 2-(4-Methoxyphenyl)propanenitrile

Temperatur

-20 °C

A solution of n-BuLi 2.0M in THF (9.7 mmoles) was slowly added to a solution of diisopropylamine (1.3 ml, 1.05 eq) and dry THF (10 ml) at −20° C. under N2. The mixture was stirred for 30 min at −20° C., then 4-methoxybenzonitrile (1.3 g, 8.8 mmoles) and dry THF (10 ml) were slowly added at −78° C. The mixture was stirred for 30 min at −78° C., then 3-(bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole (3 g, 8.8 mmoles) and dry THF (10 ml) were slowly added. The mixture was then stirred for 30 min at room temperature, poured into water, extracted with AcOEt, dried over Na2SO4, and purified by flash chromatography (AcOEt/Heptane 2/8 with 0.1% TEA) to give 3-(6-[(tert-butyl)dimethylsilyl)oxy]-1,2-benzisoxazol-3-yl)-2-(4-methoxyphenyl)propanenitrile (1 g, 28%).

1. stirringThe mixture was stirred for 30 min at −78° C.
2. stirringThe mixture was then stirred for 30 min at room temperature
3. extractionextracted with AcOEt
4. dry with materialdried over Na2SO4
5. custompurified by flash chromatography (AcOEt/Heptane 2/8 with 0.1% TEA)

ORD-Eintrag

ord-98b0d80879dc40fcb084236689d4eb1f

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08173679B2