Benzyl Bromide → HCID 18970180, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% oil dispersion, 2.1 g, 53 mmol) was added in portions to a solution of diethyl 3-hydroxycyclopentane-1,1-dicarboxylate 27 (11 g, 48 mmol), benzyl bromide (9.7 g, 53 mol), and n-tetrabutylammonium iodide (100 mg) in dry DMF (50 mL) at 25° C. (Step 25). The mixture was stirred for 1 hr at 65° C., poured onto ice and then extracted with ether (2×50 mL). The ##STR8## combined either extract was washed with water (3×50 mL) and driedover MgSO4. Chromatography on silica gel (10:90 ethyl acetate/hexane, Rf=0.38) afforded 11.6 g (75%) of the benzyl ether 28; 1H NMR (CDCl3) δ 1.3 (t, J=7.2 Hz, 6H, CH3), 1.7-2.7 (m, 6H, CH2), 4.2 (q, J=7.2 Hz, 4H, O=COCH2), 4.1 (m, 1H, O--CH), 4.6 (s, 2H, O--CH2), 7.3 (s, 5H, phenyl).

Provenance & Evidence