Tetrabutylammonium Fluoride → 3-Hydroxymethyl-5-methoxymethyl-benzonitrile
Reaktionsgleichung
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([CH2:16][O:17][CH3:18])[CH:15]=1)[C:11]#[N:12])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([CH2:16][O:17][CH3:18])[CH:15]=1)[C:11]#[N:12]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxymethyl-benzonitrile (1.402 g, 4.810 mmol) in tetrahydrofuran (10 mL) at room temperature was added tetrabutylammonium fluoride (5.051 mL, 5.051 mmol, 1 M in tetrahydrofuran). The reaction mixture was stirred at room temperature for 2 h then concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 40% ethyl acetate in hexanes yielded 3-hydroxymethyl-5-methoxymethyl-benzonitrile (713 mg, 84%).