Sodium hydride → HCID 68819124, compound

Participants

Reaction Conditions

Reaction Steps

NaH (138 mg, 3.45 mmol, 60% dispersion in oil) was added to a solution of 2-(4-bromophenyl)ethanol (833 mg, 4.1 mmol) in THF (7 mL) at 0° C. and stirred for 10 min. The mixture was cooled to −40° C. and 25A (500 mg, 1.38 mmol) in THF (7 mL) was added. After stirring warming to 0° C. over 1 h and stirring at 0° C. for 3 h the mixture was partitioned between EtOAc and brine (100 mL each). The layers were separated and the organic layer washed with 5% NaOH, brine and concentrated in vacuo. The crude solid was purified by flash chromatrography (0% to 50% EtOAc in Hexanes) to yield 26A (600 mg, 99%) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.12 (t, J=7.47 Hz, 2 H) 2.95 (t, J=6.59 Hz, 2 H) 3.38 (q, J=7.18 Hz, 2 H) 4.36 (t, J=6.59 Hz, 2 H) 7.27 (d, J=8.35 Hz, 2 H) 7.92 (dd, 1 H) 8.00 (d, 1 H) 8.08 (d, J=2.20 Hz, 1 H) 10.51 (s, 1 H).

Provenance & Evidence