1,6-Dibromohexane → 3-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

Participants

Reaction Conditions

Reaction Steps

A two phase system composed of 1,6-dibromohexane (74.06 g, 0.30 mmol) in hexanes (100 mL) and 3-methyl-3-oxetanemethanol (10.0 g, 0.10 mmol), NaOH (65.02 g, 1.63 mol), and Bu4NBr (0.5 g, 1.55 mmol) in H2O (100 mL) was stirred at 0° C. in an ice bath for 30 min. The reaction mixture was warmed up to room temperature and stirred at room temperature for 1 day. It was then heated at 100° C. for additional 2 h. The reaction mixture was allowed to cool down to room temperature and H2O was added. The mixture was extracted with hexanes three times. The combined organic phase was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude product was distilled under vacuum to give colorless liquid (b.p. 90-92° C., 0.1 mmHg) (13.75 g, 53%). 1H NMR (300 MHz, CDCl3, δ): 4.48 (d, J=5.5 Hz, 2H), 4.33 (d, J=5.9 Hz, 1H), 3.45 (s, 2H), 3.44 (t, J=6.4 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.85 (m, 2H), 1.58 (m, 2H), 1.30-1.50 (m, 4H), 1.28 (s, 3H). 13C{1H} NMR (75 MHz, CDCl3, δ): 80.17, 76.12, 71.34, 39.94, 33.71, 32.70, 29.34, 27.93, 25.34, 21.35. HRMS-FAB (m/z): [M+H]+ calcd for C11H22BrO2, 265.0803; found, 265.0802.

Provenance & Evidence