Tetrahydrofuran → HCID 86591910, compound

Participants

Reaction Steps

NaH (60% in oil, 2.4 g, 0.06 mol, approx. 1.2 eq) was placed in a dry 50 ml flask and heated to 35 degrees. To it was slowly added 50 ml of a THF solution containing 2-chloro-6-fluorobenzaldehyde (7.93 g, 0.05 mol) and methyl isocyanoacetate (5 g, 0.05 mol). The reaction was then cooled to RT, and stirred for 3 hr. At that time, 10 ml of 10% HOAc was added. After 10 min, the contents were concentrated in vacuo to a dark brown oil, then diluted with CHCl3, and transferred to a sep funnel. The aqueous phase was reextracted (3×) with CHCl3, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to crude product. Purification over a pad of silica gel was accomplished by elution with 10:1 CHCl3/EtOAc to afford the title compound, clean Z/E olefins (1:1 mix, 8.24 g, 64%).

Provenance & Evidence