Réaction #45340

Équation de réaction

[3-(methylthio)-5-(trifluoromethyl)phenyl]methanol

Dess-Martin periodinane

NaOH

→

3-(methylthio)-5-(trifluoromethyl)benzaldehyde

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   ExtractionThe mixture was extracted with EtOAc (75 mL)
2. 2
   LavageThe organic extracts were washed with brine (25 mL)
3. 3
   Séchagedried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   AutrePurification by flash chromatography with 1% to 10% EtOAc/hexanes

Mode opératoire

A solution of [3-(methylthio)-5-(trifluoromethyl)phenyl]methanol (200 mg, 0.99 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and then Dess-Martin periodinane (573 mg, 1.35 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (75 mL). The organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 1% to 10% EtOAc/hexanes afforded 3-(methylthio)-5-(trifluoromethyl)benzaldehyde. Rf=0.55 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.02 (s, 1H), 7.87 (s, 1H), 7.84 (s, 1H), 7.68 (s, 1H), 2.58 (s, 3H).

Source