Chloromethyl Methyl Ether → 1-Tetralone

Participants

Reaction Steps

2-Bromo-3-(1-methylethyl)-6-(methyloxy)-1-naphthalenol (69) (0.43 g, 1.45 mmol) was dissolved in THF (6 mL) followed by addition of diisopropylethylamine (1.02 mL, 5.78 mmol). Cooled in an ice bath, chloromethyl methyl ether (0.34 mL, 4.32 mmol) was added. The mixture was stirred at room temperature overnight. Diluted with CH2Cl2 (50 mL) and water (20 mL), and CH2Cl2 layer was separated. The aqueous layer was further extracted with CH2Cl2 (2×25 mL). The organic extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1) to give 0.43 g (79% from tetralone) of compound (70) as a light brown oil. 1H NMR (400 MHz, CDCl3): δ 1.32 (d, J=6.8 Hz, 6H), 3.49 (sept, J=6.8 Hz, 1H), 3.73 (s, 3H), 3.91 (s, 3H), 5.23 (s, 2H), 7.08 (d, J=2.4 Hz, 1H), 7.12 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.43 (s, 1H), 8.02 (d, J=9.1 Hz, 1H).

Provenance & Evidence