Hydrochloric Acid → HCID 53915561, compound

Participants

Reaction Steps

A solution of 144 g (0.91 mol) of t-butyl acetoacetate in 400 mL of tetrahydrofuran was added dropwise over 1.5 hours to a mixture of 44.0 g (1.10 mol) of sodium hydride (60% in mineral oil) in 100 mL of hexane and 500 mL of tetrahydrofuran under nitrogen at 0° C. After the addition, this mixture was stirred for 2.3 hours. A solution 2.5M n-butyllithium in hexane (360 mL, 0.91 mol) was added dropwise over 1 hour. After stirring at 0° C. for 1 hour, 200 g (0.57 mol) of the aldehyde prepared in Step A was added all at once and the temperature rose to 20° C. After stirring for 1 hour in an ice-water bath, 1200 mL of 10% aqueous hydrochloric acid was added over 1 hour. The organic layer was washed with 2×300 mL of water, 300 mL of saturated sodium chloride solution, dried with anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to give the title compound which was used without further purification.

Provenance & Evidence