Hydrochloric Acid → HCID 21480504, compound

Participants

Reaction Steps

To a stirred solution of the product from Step A (11.55 g, 41.4 mmol) in anhydrous DMF (200 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 1.74 g, 43.5 mmol). After 30 min ethyl bromoacetate (5.51 mL, 6.33 g, 49.7 mmol) was added; this solution was stirred for about 7 min and 2N HCl (100 mL) added. The resulting mixture was stirred at ambient temperature for 2 h, poured into ice-water (300 mL) and extracted with ethyl acetate (2×300 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness to give a viscous oil which was dissolved in THF (50 mL), p-TsOH (0.1 g) was added and the solution cooled on an ice bath followed by the addition of ethyl vinyl ether (7.86 mL, 82.2 mmol). After stirring for 1 h a saturated solution of sodium bicarbonate (100 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. Column chromatography (silica, 30% ethyl acetate in hexane) gave the desired product as a viscous oil (10.21 g, 63%).

Provenance & Evidence