HCID 86691458, compound → HCID 131731651, compound

Participants

Reaction Conditions

Reaction Steps

Product of Step 7 (2.5 g) was dissolved in toluene (150 mL). The solution was cooled by surrounding the flask with dry ice and the contents were stirred under argon purging for 30 min. To this was added a dispersion of ethyl lithium (25 mL, 1.7 M in butyl ether). The reaction mixture was stirred in dry ice under argon purging for 1 hr and allowed to warm to 25° C. The reaction mixture was stirred for 3 hr at 25° C. under argon purging. Then, the reaction mixture was poured in a beaker and cooled to 0° C. using an ice bath. The reaction was quenched by slow addition of water (5 mL) to the stirring toluene solution. After the evolution of gases ceased, the reaction mixture was extracted with water (three times at 50 mL each). The organic layer was diluted with ethyl acetate (500 mL) and dried over anhydrous magnesium sulfate. The organic layer was filtered and concentrated under vacuum to obtain Step 8 product as a red-brown viscous oil (3 mL). Mass spectrometry: m/z=408 (M+H). The product was carried forward without further purification.

Provenance & Evidence