Sodium methanethiolate → 2-[[2-(Methylthio)-3-pyridinyl]oxy]ethanol

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Reaction Steps

To a suspension of sodium thiomethoxide (3.01 g, 42.9 mmol) in dry DMF (30 mL) was 2-[(2-chloro-3-pyridinyl)oxy]ethanol (7.82 g, 45.1 mmol, from Example 193, Step 1) added and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between brine/1 M aqueous NaOH and CHCl3. The aqueous phase was extracted with an additional portion of CHCl3 and the combined organic layers were dried (MgSO4) and concentrated. The resulting red oil was purified by column chromatography on silica using toluene/Et3N/MeOH (96:2:2) as eluent to give 3.0 g (36%) of the title compound as brownish crystals: mp 80° C. Anal. (C7H11, NO2S)C, H, N.

Provenance & Evidence