Reaktion #48730

Reaktionsgleichung

(+/−)-trans-2-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester

triethyl-amine

sulfur trioxide pyridine

→

desired compound

(+/−)-trans-2-formyl-cyclopropanecarboxylic acid ethyl ester

Lösungsmittel

DMSO

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturWarm
2. 2
   Sonstigereaction mixture to 12° C. over 3.5 hours
3. 3
   Waschenwash with 5% aqueous citric acid (3×20 mL)
4. 4
   TrocknenDry over magnesium sulfate
5. 5
   Einengenconcentrate under reduced pressure

Vorschrift

Cool a solution of (+/−)-trans-2-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (0.22 g, 1.53 mmol) in 1.5 mL DMSO to 0° C. Add to the frozen solution triethyl-amine (0.85 mL, 0.62 mmol) followed by sulfur trioxide pyridine (0.49 g, 3.05 mmol). Warm reaction mixture to 12° C. over 3.5 hours, dilute with diethyl ether (80 mL), and wash with 5% aqueous citric acid (3×20 mL) followed by saturated aqueous sodium chloride (1×20 mL). Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound.

Quelle