Diethyl Ether → HCID 57871419, compound

Participants

Reaction Steps

Treat a mixture of trifluoromethanesulfonic acid 7-(1-ethyl-1-hydroxypropyl)naphthalen-2-yl ester (1.0 g, 2.76 mmol), Pd(OAc)2 (0.062 g, 0.27 mmol), bis-(diphenylphosphino)ferrocene (0.14 g, 0.25 mmol), Et3N (2.0 mL, 14.3 mmol) in MeOH (10 mL) and DMSO (15 mL) with carbon monoxide at 100 psi at 80° C. for 4 h. Pour the reaction mixture into ether (100 mL) and wash the resulting solution with brine (4×50 mL). Add EtOAc (100 mL), wash the organic layer with brine. Dry the organic layer over Na2SO4, filter, and concentrate the filtrate. Purify by silica gel radial chromatography (5:95 to 15:85 EtOAc:hex) to give the title compound as a yellow oil (0.71 g, 94%). 1H NMR (400 MHz, CDCl3) δ 0.792 (t, J=7.5 Hz, 6H), 1.80-2.04 (m, 4H), 4.00 (s, 3H), 7.58 (dd, J=8.8, 1.4 Hz, 1H), 7.80-7.87 (m, 2H), 7.99 (d, J=1.3 Hz, 1H), 8.02 (d, J=1.8 Hz, 1H), 8.05 (d, J=1.8 Hz, 1H), 8.61 (d, J=1.0 Hz, 1H).

Provenance & Evidence