반응 #2487438

반응 방정식

p-Toluenesulfonyl chloride

(3,5-difluoropyridin-2-yl)methanol

potassium hydroxide

→

crude material

(3,5-Difluoropyridin-2-yl)methyl 4-methylbenzenesulfonate

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added slowly at RT
2. 2
   기타After complete consumption of the starting material (by TLC)
3. 3
   workup.ADDITIONthe reaction mixture was diluted with H2O (50 mL)
4. 4
   추출extracted with EtOAc (2×25 mL)
5. 5
   세척The combined organic extracts were washed with H2O (25 mL) and brine (25 mL)
6. 6
   건조dried over anhydrous Na2SO4
7. 7
   농축concentrated under reduced pressure

실험 절차

To a solution of (3,5-difluoropyridin-2-yl)methanol (0.25 g, 0.7 mmol) in tetrahydrofuran (THF; 10 mL) was added potassium hydroxide (KOH; 0.14 g, 2.55 mmol) at RT, and the mixture was stirred for 15 min p-Toluenesulfonyl chloride (0.42 g, 2.21 mmol) was added slowly at RT, and the reaction mixture was stirred for another 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 15% EtOAc/hexane afforded compound I-5 (0.18 g, 0.25 mmol, 35%) as colorless liquid. 1H NMR (500 MHz, CDCl3): δ 8.29 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.20-7.16 (m, 1H), 5.20 (s, 2H), 2.45 (s, 3H)

출처