Dimethyl Sulfoxide → ethyl (1R,2R)-2-(3-iodophenyl)cyclopropanecarboxylate
Reaktionsgleichung
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1.[CH3:17]S(C)=O>>[I:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[CH2:17][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
Me3SOI (379 mg, 1.72 mmol) was suspended in 3 mL of DMSO. NaH (60% suspension in mineral oil, 70 mg, 1.72 mmol) was added. Stirred at room temperature before the 3-iodoethyl cinnamate (400 mg, 1.32 mmol) from Example 1A was added. The resulting mixture was heated at 65° C. for 20 minutes before it was stirred at room temperature for 2 hours. The resulting mixture was then worked up by partitioning between diethyl ether and water. The organic layer was washed with water and brine, dried over MgSO4, filtered, evaporated to provide the titled compound (127 mg, 31.8 mmol) as a light brown oil.