Lithium Bromide → HCID 63018010, compound

Participants

Reaction Steps

To a solution of 1-{[3-(methyloxy)phenyl]methyl}propyl methanesulfonate (52) (4.66 g, 18.0 mmol) in acetone (60 mL) was added LiBr (3.13 g, 36.1 mmol). The reaction mixture was refluxed under nitrogen for 8 h. Another 0.80 g of LiBr was added, and the reflux was continued for 1 h. Cooled to room temperature, the solid was filtered off and washed with acetone. The filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (100:1) to give 2.07 g (47%) of the title compound (53) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.06 (t, J=7.2 Hz, 3H), 1.70-1.82 (m, 1H), 1.83-1.95 (m, 1H), 3.10-3.20 (m, 2H), 3.80 (s, 3H), 4.10-4.20 (m, 1H), 6.75-6.85 (m, 3H), 7.22 (t, J=7.9 Hz, 1H).

Provenance & Evidence