Reaktion #791337

Reaktionsgleichung

triethylamine

dimethyl sulphoxide

3-Cyclohexyl-3-hydroxymethyloxetane

oxalyl chloride

→

3-cyclohexyl-3-formyloxetane

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added over 30 minutes
2. 2
   Sonstigequenched in water
3. 3
   ExtraktionExtraction with dichloromethane
4. 4
   Waschenby washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
5. 5
   Trocknendrying over magnesium sulphate
6. 6
   Sonstigegave a solution which
7. 7
   Sonstigewas evaporated

Vorschrift

3-Cyclohexyl-3-hydroxymethyloxetane (7.0 g) was dissolved in dry dichloromethane (20 ml) and added dropwise to a mixture of oxalyl chloride (1.1 eq, 4 ml) in dry dichloromethane (15 ml). At -70° C. a solution of dimethyl sulphoxide (7.15 ml) in dichloromethane (10 ml) was added. After stirring at -70° C. for 30 minutes triethylamine (29 ml) was added over 30 minutes. The reaction mixture was allowed to warm up to room temperature over a period of 3 hours and then quenched in water. Extraction with dichloromethane, followed by washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine and drying over magnesium sulphate gave a solution which was evaporated to give 3-cyclohexyl-3-formyloxetane as a colourless oil.

Quelle