Diisopropylamine → 2-(4-Methoxyphenyl)propanenitrile

HRID 1921273Notes

Reaction equation

[Li]CCCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18](C#N)=[CH:17][CH:16]=1.BrCC1C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2O[N:26]=1>O.C1COCC1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:10]([CH3:11])[C:12]#[N:26])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -20 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-98b0d80879dc40fcb084236689d4eb1f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173679B2

Reaction notes

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