2-Propen-1-yl 4-bromo-3,5-bis(2-propen-1-yloxy)benzoate → HCID 6709793, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 16 (30 g, 85 mmol) in THF (600 ml) at 0° C. was added lithium aluminum hydride (1.0M in THF, 175 mL, 2 equiv) dropwise over 45 minutes. The reaction was stirred at 0° C. for 2 hours, after which time saturated aqueous potassium sodium tartrate was added dropwise until bubbling ceased (25 mL, over 45 minutes). To the suspension was added ether (100 mL) and additional saturated aqueous potassium sodium tartrate (30 mL). The suspension was filtered through celite, the THF and ether were removed under reduced pressure, and water (250 mL) was added. The aqueous suspension was extracted into EtOAc (4×250 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (20→75% EtOAc/hexane) afforded 17 (11.93 g, 47%) as a white oil. Rf=0.39 (50% EtOAc/hexane); FTIR (neat, cm−1) 3363, 2924, 2869, 1587, 1435, 817; 1H NMR (400 MHz, CDCl3) δ, 6.56 (s, 2H), 6.10-6.00 (m, 2H), 5.48 (dd, J=17.4, 1.6 Hz, 2H), 5.29 (dd, J=10.6, 1.6 Hz, 2H), 4.62 (s, 2H), 4.60 (d, J=5.2 Hz, 4H); 13C NMR (100 MHz, CDCl3) δ156.2, 141.4, 132.6, 117.6, 104.5, 100.9, 69.8, 65.0; MS EI+ calculated for C13H15BrO3 (M−H)+: 298, found: 298.

Provenance & Evidence