Reaktion #2294236

Reaktionsgleichung

(S)-2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

triethylamine

→

(S)-2-(5-bromo-2-formyl-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Lösungsmittel

DCM DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched with ice-water
2. 2
   ExtraktionThe water phase was extracted with ethyl acetate
3. 3
   WaschenThe organic phase was washed with saturated sodium bicarbonate solution, water and brine
4. 4
   Trocknenwas dried over sodium sulfate
5. 5
   EinengenConcentration

Vorschrift

To a solution of (S)-2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate (180 mg, 0.4 mmol) in DCM/DMSO (0.5 ml/0.5 ml) at 0° C. was added triethylamine (192 μl), followed by SO3-pyridine (222 mg). The mixture was stirred for 1 hour, and was quenched with ice-water. The water phase was extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate solution, water and brine, and was dried over sodium sulfate. Concentration gave (S)-2-(5-bromo-2-formyl-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate. ESI+ (m/z): [M+H]+ calc'd for C22H29BrNO4: 450.1; Found: 450.2.

Quelle