1-Butanol → 2-Butoxy-1,3-thiazole

Participants

Reaction Steps

A suspension of NaH (6.7 mmol, 0.27 g, 60% dispersion) in dry DMF was stirred with butanol (6.09 mmol, 0.55 mL) under argon until evolution of hydrogen ceased. 2-Bromothiazole (6.09 mmol, 0.55 mL) was added and after 15 minutes the mixture was heated to reflux. After 48 hours the reaction was quenched with water and extracted with ethyl acetate (4x). The organic phases were combined, dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (hexane followed with 1% ethyl acetate) to afford 0.35 g (37%) of 2-(1-butoxy)thiazole as an amber oil.

Provenance & Evidence