Reaktion #53396

Reaktionsgleichung

allyl bromide

Potassium tert-butoxide

29

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

→

compound 30

Ausbeute 71.0%

N-Cbz-4-(4-Allyloxyphenyl)butylamine

Ausbeute 71.0%

Lösungsmittel

MeCN

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
2. 2
   Filtrationthe precipitate was filtered off
3. 3
   Waschenwashed with ethyl acetate
4. 4
   Sonstigethe solvent was removed at reduced pressure
5. 5
   Sonstigethe residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes)

Vorschrift

Potassium tert-butoxide (1.7 g, 15.2 mmol) and 18-crown-6 (0.1 g, 0.3 mmol) were added to a solution of 29 (4.3 g, 14.3 mmol) in dry MeCN (80 mL) and the mixture was stirred for 20 min at room temperature. After this time, allyl bromide (1.2 mL, 14.3 mmol) in MeCN (10 mL) was added. The reaction mixture was stirred overnight at room temperature, then the precipitate was filtered off and washed with ethyl acetate. The organic fractions were combined, the solvent was removed at reduced pressure and the residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes) to provide compound 30 (3.4 g, 71%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.55 (m, 4H), 2.54 (t, 2H), 3.20 m, 2H), 4.50 (d, 2H), 5.08 (s, 2H), 5.28 (d, 1H), 5.40 (d, 1H), 6.06 (m, 1H), 6.82 (d, 2H), 7.05 (d, 2H), 7.33 (s, 5H).

Quelle