تفاعل #45333

معادلة التفاعل

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

Dess-Martin periodinane

NaOH

→

3-nitro-5-(trifluoromethyl)benzaldehyde

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted with EtOAc (50 mL)
2. 2
   غسيلthe organic extracts were washed with brine (25 mL)
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification by flash chromatography with 0% to 15% EtOAc/hexanes

الإجراء التجريبي

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).

المصدر