Sodium hydride → HCID 70795677, compound

Participants

Reaction Steps

Ring closure of alcohol 84 with NaH as in Example 2A at 0° C. for 80 min and then at 17° C. for 60 min, followed by chromatography of the product on silica gel, eluting with 0-40% EtOAc/petroleum ether (foreruns) and then with 40% EtOAc/petroleum ether and 0-0.5% MeOH/CH2Cl2, gave 2-[(4-iodophenoxy)methyl]-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole (85) (77%) as a pale yellow solid: mp (MeOH/CH2Cl2/hexane) 198-199° C.; 1H NMR [(CD3)2SO] δ 8.15 (s, 1H), 7.61 (dt, J=8.9, 2.6 Hz, 2H), 6.80 (dt, J=9.0, 2.6 Hz, 2H), 5.72 (m, 1H), 4.49 (dd, J=10.7, 9.0 Hz, 1H), 4.41 (dd, J=11.6, 2.7 Hz, 1H), 4.35 (dd, J=11.6, 5.2 Hz, 1H), 4.20 (dd, J=10.8, 6.5 Hz, 1H). Anal. (C12H10IN3O4) C, H, N.

Provenance & Evidence