반응 #80461

반응 방정식

2-(3-pyridylhydroxymethyl)thiophene

tin(II)chloride dihydrate

HCl

→

2-(3-pyridylmethyl)thiophene

수율 32.5%

용매

acetic acid

반응 조건

후처리

1. 1
   기타was bubbled through the reaction mixture for about 10 min
2. 2
   기타the liquid was decanted
3. 3
   농축concentrated in vacuo to a volume of about 10 mL
4. 4
   workup.ADDITIONpoured into H2O
5. 5
   workup.ADDITIONThe aqueous solution was made basic by the slow addition of saturated aqueous NaHCO3
6. 6
   추출extracted with ethyl acetate/ether
7. 7
   건조The organic phase was dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

To a solution of 2-(3-pyridylhydroxymethyl)thiophene (8.82 g, 46.2 mmol), prepared as in step 1, in acetic acid (50 mL) was added tin(II)chloride dihydrate (22.9 g, 101 mmol) and HCl gas was bubbled through the reaction mixture for about 10 min. The reaction mixture was stirred for 1.5 hours at ambient temperature, and the liquid was decanted, concentrated in vacuo to a volume of about 10 mL, and poured into H2O. The aqueous solution was made basic by the slow addition of saturated aqueous NaHCO3 and extracted with ethyl acetate/ether. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (5% methanol/CHCl3) gave 2-(3-pyridylmethyl)thiophene (2.63 g).

출처