Sodium hydride → HCID 10754259, compound

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 525 mg, 13 mmol) was added to a round bottom flask and washed with 3×5 mL of dry hexane. Dry THF (25 mL) was then added, followed by 2-phenyl-1,3-propanediol (2.0 g, 13 mmol). Another 25 mL of dry THF was added to facilitate stirring of the resulting thick suspension. After 45 min., tert-butyldimethylsilyl chloride was added in one portion. After stirring for 2 h, the mixture was partitioned between 100 mL of ethyl ether and 60 mL of 10% aqueous potassium carbonate. The aqueous layer was extracted with 2×30 mL of ethyl ether. The combined organic layers were washed with 40 mL of brine, dried over sodium sulfate, and evaporated. Purification by flash column chromatography, eluting with 10% ethyl acetate in hexane, gave the 3.36 g of the title compound as a colorless liquid. 1NMR (400 MHz,CD3OD): δ 7.30-7.16(m, 5H), 3.90 (dd, 1H, J=11, 7 Hz), 3.88 (dd, 1H, J=10, 6 Hz), 3.83 (dd, 1H, J=10, 6 Hz), 3.76 (dd, 1H, J=11, 7 Hz), 2.91 (quintet, 1H, J=6 Hz), 0.84 (s, 9H),-0.04 (s, 3H),-0.05 (s, 3H). Mass spectrum (NH3 /CI): m/z=267 (M+1).

Provenance & Evidence