Reaktion #1960776

Reaktionsgleichung

triethylamine

oxalyl chloride

dimethyl sulfoxide

sodium bicarbonate

compound

(cis-4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)methanol

→

cis-4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexanecarbaldehyde

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGis stirred at −78° C. for 1 h
2. 2
   workup.WAITOver a period of one hour
3. 3
   Temperaturthe reaction mixture is then warmed to RT
4. 4
   SonstigeThe phases are separated
5. 5
   Trocknenthe organic phase is dried over sodium sulfate
6. 6
   Sonstigethe solvent is removed on a rotary evaporator
7. 7
   SonstigeThe residue is purified chromatographically on silica gel 60 (mobile phase: gradient petroleum ether→petroleum ether/ethyl acetate 9:1)

Vorschrift

16.4 g (129.47 mmol) oxalyl chloride are dissolved in 600 ml of dichloromethane and cooled to −78° C. 20.2 g (258.95 mmol) of dimethyl sulfoxide are then slowly added dropwise. The mixture is stirred for 5 min. After addition of a solution of 21.1 g (86.32 mmol) of the compound from Example 53A in 200 ml of dichloromethane the mixture is stirred at −78° C. for 1 h. 60 ml (431.58 mmol) of triethylamine are then slowly added dropwise. Over a period of one hour, the reaction mixture is then warmed to RT, and 500 ml of saturated aqueous sodium bicarbonate solution are then added. The phases are separated, the organic phase is dried over sodium sulfate and the solvent is removed on a rotary evaporator. The residue is purified chromatographically on silica gel 60 (mobile phase: gradient petroleum ether→petroleum ether/ethyl acetate 9:1).

Quelle