Sodium hydride → HCID 59011464, compound

Participants

Reaction Steps

To a solution of 2 (88.96 g, 0.27 mol) in DME (1 L) at RT under N2 was added (carefully) NaH (60% in mineral oil, 31.92 g, 0.80 mol) to give a dark violet solution. The reaction was heated at reflux for 4 h, was cooled and quenched carefully with H2O, acidified with 2N HCl and extracted with 2×EtOAc. The combined organics were washed with saturated NaCl solution, dried over a mixture of activated charcoal and Na2SO4, filtered through Celite and evaporated to give crude product 3 as a brown solid (83.42 g, >100%). 1H-NMR (500 MHz, dmso-d6) 12.1 (s, 1H), 8.31 (d, 2H), 7.88 (d, 2H), 3.75 (s, 3H), 2.86 (AB quartet, 2H), 2.65 (m, 1H), 2.6 (m, 1H), 2.4 (m, 1H), 2.35 (m, 1H) ppm.

Provenance & Evidence