Hydrochloric Acid → 3-[(Thiophen-2-yl)methyl]pyridine

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(H)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).

1. customwas bubbled through the reaction mixture for about 10 min
2. customthe liquid was decanted
3. concentrationconcentrated in vacuo to a volume of about 10 mL
4. additionpoured into H2O
5. additionThe aqueous solution was made basic by the slow addition of saturated aqueous NaHCO3
6. extractionextracted with ethyl acetate/ether
7. dry with materialThe organic phase was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-69af6c1fa95b48d8ac8a8b9d8ae1aacb

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506261