Sodium hydride → HCID 67003370, compound

Participants

Reaction Steps

To an ambient suspension of sodium hydride (1.136 g, 47.3 mmol) in N,N-dimethylformamide (126 ml) was added 2,2-dimethyl-5-(thiazol-2-yl)-1,3-dioxan-5-ol (Example 11A) (8.15 g, 37.9 mmol) as a solution in N,N-dimethylformamide (20 mL). The reaction was stirred for 30 minutes, and tetrabutylammonium iodide (0.699 g, 1.893 mmol) and 1-(chloromethyl)-4-methoxybenzene (6.42 ml, 47.3 mmol) were sequentially added. The reaction was stirred overnight and then quenched by the addition of saturated aqueous ammonium chloride solution and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 40% ethyl acetate in hexane, to give the title product. MS ESI(+) m/z 336.0 [M+H]+.

Provenance & Evidence