Tetrahydrofuran → HCID 59389357, compound

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Reaction Steps

The compound of Example 349 (11.09 g) was dissolved in tetrahydrofuran (320 mL) in an argon atmosphere. While this solution was chilled in a ice salt water bath (−7° C.), ethyl magnesium bromide (100 mL, 0.91 mol/L tetrahydrofuran solution) was added dropwise and the mixture was stirred at room temperature for 1 hour. Subsequently, a saturated aqueous ammonium chloride solution was added while the mixture was chilled in an ice bath. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel chromatography (hexane:ethyl acetate=2:3→1:2→1:4→ethyl acetate) afforded the title compound as a yellow powder (4.21 g).

Provenance & Evidence