Tetrahydrofuran → 1-Naphthol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of isopropylcyclohexylamine (7.5 mL, 0.45 mmol) in 60 mL of THF at -78° C. under N2 was added n-BuLi (20.0 mL, 50.0 mmol, 2.5M in hexanes). The mixture was stirred for 20 min, warmed to 0° C., and then stirred for 1 h. The mixture was cooled to -78° C. and solution of N,N-diethyl-3,3-dimethylacrylamide (2.10 g, 13.0 mmol) in 40 mL of THF was added. This mixture was stirred at -78° C. for 1 h. The cold bath was removed and the reaction mixture was allowed to warm to -20° C. over a period of 10 min. A solution of 2,4-dibromo-1-methoxymethoxybenzene (9) in 30 mL of THF was added. The reaction mixture was stirred overnight at room temperature, and then quenched with saturated NH4Cl Et2O was added and the solution was washed with H2O, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by flash chromatography (hexanes/EtOAc; 9:1) to yield napthol 12 (1.15 g, 29%) as a brown oil; 1H NMR (CDCl3, 300 MHz): δ9.31 [s, OH], 7.54 [d, J=8.4 Hz, ArH(6)], 7.49 [s, ArH(4)], 6.82 [s, ArH(2)[, 6.81 [d, J=8.4 Hz, ArH(7)], 5.46 [s, OCH2OCH3 ], 3.55 [s, OCH3 ], and 2.47 [s, ARCH3 (3)]; 13C NMR (CDCl3, 75 MHz): 67 154.3, 153.5, 139.5, 134.5, 129.6, 118.2, 115.5, 114.5, 113.6, 107.3, 95.9, 56.9, and 22.0; LRMS (EI): m/z 298 (M+, 13), 296 (M+, 11), 128 (5), 115 (9), and 45 (100).

Provenance & Evidence