Reaktion #648986

Reaktionsgleichung

propyl 2-[(1E)-3-methoxyprop-1-en-1-yl]quinoline-4-carboxylate

→

title compound

Propyl 2-(3-methoxypropyl]quinoline-4-carboxylate

Lösungsmittel

EtOAc

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed sequentially with water, sat. aq. NaHCO3 and brine
2. 2
   TrocknenDrying over MgSO4, filtration and concentration of the filtrate in vacuo
3. 3
   Sonstigeafforded the crude product as a yellow oil
4. 4
   SonstigePurification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Vorschrift

To a solution of propyl 2-[(1E)-3-methoxyprop-1-en-1-yl]quinoline-4-carboxylate from the previous step (1 eq.) in toluene (0.06 M) was added at 80° C. benzenesulfonyl hydrazide (3×1 eq.) over 3 h. The reaction mixture was diluted with EtOAc and washed sequentially with water, sat. aq. NaHCO3 and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Quelle