Reaktion #45333

Reaktionsgleichung

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

Dess-Martin periodinane

NaOH

→

3-nitro-5-(trifluoromethyl)benzaldehyde

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with EtOAc (50 mL)
2. 2
   Waschenthe organic extracts were washed with brine (25 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash chromatography with 0% to 15% EtOAc/hexanes

Vorschrift

A solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (400 mg, 1.88 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and then Dess-Martin periodinane (1.59 g, 3.76 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 (50 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 15% EtOAc/hexanes afforded 3-nitro-5-(trifluoromethyl)benzaldehyde. Rf=0.39 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.18 (s, 1H), 8.91 (s, 1H), 8.74 (s, 1H), 8.48 (s, 1H).

Quelle