Sodium Bicarbonate → 5-Fluoromethyl-2-methoxymethoxymethylpyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 70% HF-pyridine complex (0.3 ml) is added to a solution of morpholinosulfur trifluoride (2 ml, 1.63×10−2 mol) in dichloromethane (32 ml) cooled to −78° C. and maintained under an inert atmosphere, followed by dropwise addition of 1 g (5.4 mmol) of compound (3) as a solution in CH2Cl2 (10 ml). The mixture is stirred for 2 hours at −78° C. and then poured into saturated NaHCO3 solution (75 ml). The aqueous phase is extracted with dichloromethane and the combined organic phases are washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue is bulb-to-bulb distilled (P: 4.7×10−2 mb, b.p.: 110-130° C.). The title compound is isolated in the form of a colorless oil (0.3 g), which is used directly in the following step.

Provenance & Evidence