Benzyl Bromide → HCID 23256317, compound

Participants

Reaction Steps

A solution of 2.13 (0.140 g, 1.0 mmol) in DMF (5 mL) was stirred with silver(I) oxide (0.232 g, 1.0 mmol) and benzyl bromide (0.3 mL, 2.5 mmol) for 5 days at room temperature. The reaction mixture was filtered, diluted with water, and extracted thrice with EtOAc. The organic layer was washed with water, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography over silica gel with hexanes:EtOAc (2:1) as eluant to give the intermediate 5-[(benzyloxy)methyl]-5-vinyl-tetrahydro-2-furanone (0.186 g, 80%) as an oil; [α]22D -29.68° (c 3.08, CHCl3); IR (neat) 1772 (C=O) and 1653 cm-1 (C=C); 1H NMR (CDCl3) δ 2.05 (m, 1 H, H-4a), 2.35-2.74 (m, 3 H, H-4b, H-3), 3.55 (AB q, J=10.4 Hz, 2 H, CH2OH), 4.60 (AB q, J=12.0 Hz, 2 H, CH2OCH2Ph), 5.22 (dd, J=10.9, 0.5 Hz, 1 H, CH=CHH), 5.37 (dd, J=17.3, 0.6 Hz, 1 H, CH=CHH), 5.88 (dd, J=17.3, 10.9 Hz, 1 H, CH=CH2); 13C NMR (CDCl3) δ 28.88, 29.37, 73.66, 74.50, 86.81, 115.73, 127.58, 127.80, 128.46, 136.72, 137.65, 176.82. Anal. Calcd for C14H16O3 : C, 72.39; H, 6.94. Found: C, 72.62; H, 6.92.

Provenance & Evidence