Triethylamine → 2,3-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)pyridine

Participants

Reaction Steps

A mixture of (5,6-dichloro-3-pyridinyl)methanol (2000 mg, 11.23 mmol), Et3N (2.349 ml, 16.85 mmol), and tert-butyldimethylsilyl chloride (1778 mg, 11.80 mmol) in DMF (20 ml) was stirred at room temperature for 4 h. HPLC analyse showed starting material remaining, an excess of tert-butyldimethylsilyl chloride (847 mg, 5.62 mmol) and Et3N (1.174 ml, 8.43 mmol) were added. The mixture reaction was stirred overnight. The crude was diluted with TBME (175 mL) and water. The organic phase was washed with solution sat. NaCl. Combined organics were washed with sat NH4Cl and dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography using Flashmaster II, a 50 g silica gel cartridge, and mixtures of hexane and EtOAc as eluent afforded 2,3-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)pyridine 2.5 g (72%) of a yellow oil.

Provenance & Evidence