Reaktion #426248

Reaktionsgleichung

2-methylquinolin-7-ol

PPh3

(S)-2-methoxypropan-1-ol

diisopropyl azodicarboxylate

HCl

→

(S)-7-(2-methoxypropoxy)-2-methylquinoline

Ausbeute 51.0%

Lösungsmittel

THF

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then heated at 50° C. for additional 2 hours
2. 2
   TemperaturAfter cooling, to the reaction
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Waschenwashed with EtOAc (100 mL)
5. 5
   Extraktionextracted with EtOAc
6. 6
   Waschenwashed with brine
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe residue was purified by flash chromatography on silica gel (1:1 hexane/EtOAc)

Vorschrift

To a stirred solution of 2-methylquinolin-7-ol (1.00 g, 6.28 mmol), PPh3 (4.12 g, 15.7 mmol) and (S)-2-methoxypropan-1-ol (0.679 g, 7.54 mmol) in THF (60 mL) was added dropwise diisopropyl azodicarboxylate (2.05 mL, 10.1 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at ambient temperature overnight. The reaction was then heated at 50° C. for additional 2 hours. After cooling, to the reaction were added 4N HCl (3.1 mL), water (100 mL) and EtOAc (200 mL). The aqueous layer was separated and washed with EtOAc (100 mL). The aqueous was neutralized with ammonium hydroxide to about pH 9, extracted with EtOAc, washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:1 hexane/EtOAc) to give (S)-7-(2-methoxypropoxy)-2-methylquinoline (0.738 g, 51%).

Quelle