تفاعل #358643

معادلة التفاعل

(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol

thionyl chloride

→

title compound

المردود 93.2%

3-(chloromethyl)-2-cyclopropyl-6-(trifluoromethyl)pyridine

المردود 93.2%

المذيبات

dichloromethane

EtOAc

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was then concentrated under vacuum
2. 2
   أخرىto obtain a light brown oil
3. 3
   غسيلwashed with 10% aqueous Na2CO3 solution (20 mL)
4. 4
   أخرىThe organic layer was separated
5. 5
   غسيلwashed with saturated aqueous NaCl
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated

الإجراء التجريبي

To a stirring solution of (2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol (890 mg, 4.1 mmol) in dichloromethane (10 mL) at room temperature under argon was added thionyl chloride (730 mg, 6.1 mmol) followed by 3 drops of DMF. The reaction mixture was stirred at room temperature for 15 h. The reaction mixture was then concentrated under vacuum to obtain a light brown oil. This oil was diluted with EtOAc (20 mL) and washed with 10% aqueous Na2CO3 solution (20 mL). The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain 900 mg of the title compound as a light brown oil. HPLC/MS: retention time=3.66 min, [M+H]+=236.

المصدر