تفاعل #513294

معادلة التفاعل

2-Chloro-6-methyl-isonicotinic acid

HCl

NaOH

→

pale yellow solid

المردود 71.0%

(2-Chloro-6-methyl-pyridin-4-yl)-methanol

المردود 71.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added 1M borane-methyl sulfide complex (6 ml, 60 mmol)
2. 2
   درجة الحرارةThe mixture was cooled in an ice bath
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   استخلاصThe product was extracted with dichloromethane
5. 5
   تجفيفdried with anhydrous potassium carbonate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated in vacuo
8. 8
   أخرىThe crude product was purified by silica gel column chromatography (eluent, methanol:dichloromethane (5:95))

الإجراء التجريبي

To a stirred solution of 2-Chloro-6-methyl-isonicotinic acid (2 g, 11.65 mmol) in anhydrous THF (40 ml) cooled in an ice bath, was added 1M borane-methyl sulfide complex (6 ml, 60 mmol). After 1 hr, the mixture was stirred for 48 hr at room temperature. The mixture was cooled in an ice bath and conc. HCl (18 ml) was added and stirred for 30 min. The mixture was then basified by addition of 50% aqueous NaOH (15 ml). The product was extracted with dichloromethane, dried with anhydrous potassium carbonate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent, methanol:dichloromethane (5:95)) to afford 1.3 g (71%) of a pale yellow solid; m.p. 112-113° C.; 1H NMR (200 MHz, CDCl3) δ 2.26 (1H, t, J=5.4 Hz), 2.52 (3H, s), 4.70 (2H, d, J=5.4 Hz), 7.15 (1H, s), 7.16 (1H, s); m/z (EI) 157 (M+).

المصدر