1-Acetoxy-2-bromoethane → HCID 59389387, compound

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Reaction Steps

60% sodium hydride (135 mg) was added to a solution of the compound of Example 180 (830 mg) in N,N-dimethylformamide (40 mL) in a stream of argon gas while the solution was stirred in an ice bath. The mixture was then stirred at room temperature for 15 min. Subsequently, bromoethyl acetate (374 μL) was added to the mixture under stirring in an ice bath. The mixture was further stirred at room temperature for 3 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (×2) and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=2:1) afforded the title compound as a mixture with o-alkylated form. This product was used in the subsequent reaction without further purification.

Provenance & Evidence