Ammonium Chloride → HCID 20145559, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 50 ml of 2M ethylmagnesium bromide in tetrahydrofuran at 0° C. was added a solution of 1-oxo-2-methylhex-4-yne in 20 ml of tetrahydrofuran. The mixture was stirred for 11/2 hour at 0° C., poured into saturated ammonium chloride solution, and extracted three times with diethyl ether. The combined extracts were washed with brine, dried over anhydrous sodium sulfate and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane, to give 6.0 g of 3-hydroxy-4-methyloct-1,6-diyne, the compound of formula (LXV).

Provenance & Evidence