Reaktion #1906633

Reaktionsgleichung

quinolin-5-yl-methanol

DPPA

DBU

→

5-azidomethyl-quinoline

Ausbeute 44.3%

Lösungsmittel

HCl

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated
2. 2
   Extraktionthe aqueous phase was re-extracted with ethyl acetate (×2)
3. 3
   TrocknenThe combined organic phase was dried over Na2SO4
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting residue was purified by silica gel prep TLC

Vorschrift

To a solution of quinolin-5-yl-methanol (96 mg, 0.60 mmol) and DPPA (202 μL, 0.91 mmol) in toluene (2 mL) was added DBU (166 μL, 1.09 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with 3M HCl (1.7 mL) and ethyl acetate (5 mL). The organic phase was separated and the aqueous phase was re-extracted with ethyl acetate (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 49 mg of 5-azidomethyl-quinoline as light brown oil (44%).

Quelle