Sodium hydride → HCID 67407442, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 113 (2.6 g) in DMF (20 mL) was cooled to 0° C. NaH (60%, 0.28 g, 6.91 mmol) was added in one portion. After 10 min, the reaction mixture was carefully quenched by the addition of saturated aqueous NH4Cl. The mixture was diluted with diethyl ether and water and the layers were separated. The ether layer was washed five times with water to remove DMF then once with brine. The combined aqueous washes were back-extracted with diethyl ether. The combined ether extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.59 g of crude 114 which was used without further purification. 1H NMR (300 MHz, CDCl3): δ7.36 (m, 5H), 5.15 (m, 2H), 4.35 (m, 2H), 3.77-3.66 (m, 2H), 3.26-3.14 (m, 2H), 2.26 (m, 1H), 2.23 (m, 1H), 1.94 (m, 2H), 1.46 (s, 9H) ppm.

Provenance & Evidence