Dimethylformamide → HCID 25150126, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxymethylbenzyl)phenol (1.00 g, 3.18 mmol, Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000)) in DMF (30.0 mL) was added Cs2CO3 (5.18 g, 15.90 mmol) followed by 1,2-dibromoethane (1.64 g, 19.08 mmol). The reaction mixture was stirred at 60° C. for 2 d, diluted with ethyl acetate and washed with water (20 mL×4) and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:19) to afford 1-(2-bromoethoxy)-4-(3′-iso-propyl-4′-methoxymethoxybenzyl)-3,5-dimethylbenzene as an oil (0.26 g, 16%): 1H NMR (300 MHz, CDCl3): δ 6.94 (m, 2H), 6.67 (m, 3H), 5.18 (s, 2H), 4.32 (m, 2H), 3.95 (s, 2H), 3.68 (m, 2H), 3.51 (s, 3H), 3.37 (s, 3H), 3.32 (m, 1H), 2.26 (s, 6H), 1.22 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (4:1); Rf=0.91.

Provenance & Evidence