Hydrochloric Acid → HCID 11393125, compound

Participants

Reaction Steps

DIBAL-H (1.0 M, 3.84 mL, 3.84 mmol) was added to a solution of ethyl 2-[4-benzyloxy-2-nitronaphthalen-1-yl]acetate (0.35 g, 0.96 mmol) in THF (4 mL) slowly under N2 atmosphere at 0° C., and stirred for 15 min. The mixture was poured into chilled 1 N HCl (10 mL) slowly, and the mixture was extracted with AcOEt (50 mL). The organic layer was washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL), and then the organic layer was dried (Na2SO4) and evaporated to yield 2-[4-benzyloxy-2-nitronaphthalen-1-yl]ethanol (0.33 g, quant.) as a dark brown solid. Mp 82-90 ° C.; 1H NMR (CDCl3, 500 MHz) δ 8.43 (d, 8.5, 1H), 8.25 (d, 9.0, 1H), 7.71 (t, 7.0, 1H), 7.65 (t, 7.0, 1H), 7.54 (d, 8.0, 2H), 7.45 (t, 7.5, 2H), 7.40 (t, 7.0, 1H), 7.19 (s, 1H), 5.29 (s, 2H), 4.08 (t, 6.5, 2H), 3.49 (t, 6.5, 2H); EIMS m/z 323 (M+); IR (neat) νmax 3368, 2929, 1593, 1526, 1513, 1463, 1423, 1363, 1337, 1271, 1240, 1161, 1103, 1039, 829, 755, 697 cm−1.

Provenance & Evidence