반응 #7273

반응 방정식

3-methylsulfanyl-pyridine-2-carbaldehyde

oxone

→

3-methanesulfinyl-pyridine-2-carbaldehyde

수율 23.0%

용매

MeOH

water

CH2Cl2

반응 조건

후처리

1. 1
   여과filtered through celite
2. 2
   세척washed with CH2Cl2 (3×20 mL)
3. 3
   농축concentrated
4. 4
   기타dried in vacuo
5. 5
   기타Flash chromatography (silica gel, 4:1 hexanes-EtOAc) of the residue thus obtained

실험 절차

To a cold (0° C.), stirred solution of 3-methylsulfanyl-pyridine-2-carbaldehyde (prepared as described for AMD9574) (280 mg, 1.83 mmol) in a mixture of MeOH (20 mL) and water (2 mL) was added solid oxone (2.25 g, 3.66 mmol) and the resulting heterogeneous mixture was stirred for 5 h. At this point, the reaction mixture was diluted with CH2Cl2 (50 mL), and then filtered through celite, washed with CH2Cl2 (3×20 mL) and concentrated and dried in vacuo. Flash chromatography (silica gel, 4:1 hexanes-EtOAc) of the residue thus obtained afforded 70 mg (23%) of 3-methanesulfinyl-pyridine-2-carbaldehyde. 1H NMR (CDCl3) □ 2.86 (s, 3H), 7.81 (dd, 1H, J=8, 5 Hz), 8.66–8.69 (m, 1H), 8.90 (d, 1H, J=3 Hz), 10.12 (s, 1H).

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