Reaktion #348158

Reaktionsgleichung

allyl bromide

Trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane

trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

18-crown-6

potassium carbonate

→

Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Ausbeute 95.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 10% HCl
2. 2
   Extraktionextracted with diethyl ether
3. 3
   TrocknenThe organic layer was dried over MgSO4
4. 4
   Einengenconcentrated to a yellow oil in vacuo which
5. 5
   Sonstigewas purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent

Vorschrift

Trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane (21) (2.50 g, 5.69 mmole) was dissolved in 30 ml dry DMF and allyl bromide (0.963 g, 7.97 mmole) was added by syringe. To this solution was added 100 mg of 18-crown-6 and potassium carbonate (0.785 g, 5.69 mmole). The reaction was stirred at 50° C. under an argon atmosphere for 4 hours. The reaction was quenched with 10% HCl and extracted with diethyl ether. The organic layer was dried over MgSO4, and concentrated to a yellow oil in vacuo which was purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent. (2.60 g, 95% yield: colorless oil).

Quelle