Reaktion #53408

Reaktionsgleichung

2-bromoethyl methyl ether

29

N-Cbz-4-(4-Hydroxyphenyl)butylamine

sodium hydride

→

64

Ausbeute 66.7%

N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamine

Ausbeute 66.7%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   SonstigeThe solvent was removed under reduced pressure
3. 3
   Sonstigethe material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate)

Vorschrift

To a vigorously stirred solution of 29 (4 g, 0.013 mol) in anhydrous THF (150 mL) under nitrogen at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.64 g, 0.016 mol). The mixture was stirred for 15 min then tetrabutylammonium iodide (0.5 g, 0.0013 mol) and 2-bromoethyl methyl ether (2.04 g, 0.015 mol) were added and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate) to provide 64 (3.1 g, 64%). 1H NMR (300 MHz, CDCl3) δ 1.60 (m, 4H), 2.59 (m, 2H), 3.23 (m, 2H), 3.45 (s, 3H), 3.77 (m, 2H), 4.10 (m, 2H), 5.13 (s, 2H), 6.88 (d, 2H), 7.08 (d, 2H), 7.47 (s, 5H).

Quelle