Reaktion #988243

Reaktionsgleichung

compound 1

2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

CH2Cl2

DMSO

sulfur trioxide-pyridine

→

solid

Ausbeute 52.0%

(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehyde

Ausbeute 52.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with Et2O
2. 2
   TrocknenThe combined organic phases were dried with Na2SO4
3. 3
   Einengenconcentrated
4. 4
   Sonstigepurified by column chromatography

Vorschrift

To a stirred solution of compound 1 (136 mg, 0.5 mmol), CH2Cl2 (2 mL), dry DMSO (142 μL, 2.0 mmol, 4.0 eq), and dry TEA (697 μL, 5.0 mmol, 10.0 eq) at room temperature under argon, sulfur trioxide-pyridine complex (Pyr-SO3, 318 mg, 2.0 mmol, 4.0 eq) was added in a portion-wise manner and stirred for two days. The resulting mixture was then diluted with water and extracted three times with Et2O. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 20:80:EtOAc:Hexane to give a yellow-white solid (70 mg, 52%). Spectral data were identical to those reported above.

Quelle