2,6-Dichloropyridine → 2-Chloro-6-(2-Thienylmethoxy)Pyridine

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[N:10]=1>O1CCOCC1.CCCCCC.C(OCC)(=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[N:10]=1

Komponenten

Versuchsvorschrift

K-t-BuO (1.70 g, 15.1 mmol) was added portionwise to a stirred mixture of 2-thiophenemethanol (2.14 g, 18.7 mmol) and 2,6-dichloropyridine (2.13 g, 14.4 mmol) in dioxane (3 mL) at room temperature. An exotermic reaction started and more dioxane (3 mL) was added. After 3 h of stirring at room temperature, the reaction mixture was passed through a column of silica using n-hexane/ethyl acetate (85:15) as eluent. A second purification on silica (16×4 cm) using n-hexane/ethyl acetate (9:1) firnished 3.0 g (93%) of the title compound as a light beige oil. HRMS m/z calcd for C10H8ClNOS (M)+ 225.0015, found 225.0022. Anal. (C10H8CINOS) C, H, N. *Previously described in EP 693490.