2-(Trimethylsilyl)ethanol → HCID 59526323, compound

Participants

Reaction Conditions

Reaction Steps

2-(Trimethylsilyl)ethanol (5.05 mL, 35.2 mmol) was taken up in THF (50 mL) and cooled to 0° C. Sodium hydride (1.48 g, 36.9 mmol) was added in 3 portions and the resulting mixture stirred at 0° C. for 15 minutes. This suspension was then added to a solution of 3,6-Dichloropyridazine (5 g, 33.6 mmol) in THF (50 mL) at 0° C. After stirring at 0° C. for 30 minutes, room temperature was attained and stirring continued overnight. Water was added followed by saturated NH4Cl and the reaction mixture was extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (2-20% EtOAc-hexanes) gave the title compound as a white solid.

Provenance & Evidence