Water → HCID 25132944, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1 (7.02 g, 27.32 mmol) and 2-(2-bromoethyl)-1,3-dioxolane compound 2 (3.85 mL, 32.78 mmol) in anhydrous DMF (100 mL), potassium t-butoxide (32.78 mL, 1 M in t-BuOH) was added. The content was heated to 80° C. and stirred overnight. H2O (400 mL) and brine (200 mL) were added to the content and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. Flash column chromatography with hexane/ethyl acetate (6/1) afforded 9.5 g brown oil (˜85% product+˜15% SM). 1H NMR (400 MHz, CDCl3) δ[ppm]: 7.66 (1H, d, J=2.3 Hz), 7.48 (1H, d, J=8.4 Hz), 7.40 (1H, dd, J=8.4 Hz, 2.2 Hz), 4.91 (1H, t, J=4.4 Hz), 4.30-4.20 (2H, m), 3.98-3.94 (2H, m), 3.86-3.83 (2H, m), 2.48 (1H, td, J=12.2 Hz, 4.5 Hz), 2.24 (1H, td, J=12.2 Hz, 4.3 Hz), 1.88-1.81 (1H, m), 1.75-1.68 (1H, m), 1.24 (3H, t, J=7.1 Hz). 13C NMR (400 MHz, CDCl3) δ[ppm]: 166.90, 134.68, 133.70, 131.28, 128.60, 125.88, 117.58, 103.04, 65.26, 63.91, 53.22, 32.24, 29.88, 14.06.

Provenance & Evidence