Dimethylformamide → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% oil dispersion, 2.2 g, 56 mmol) was added in portions to a solution of 6-hydroxycyclohexanone ethylene ketal (39) (8.8 g, 51 mmol), benzyl bromide (9.6 g, 5.6 mmol), and tetra-n-butylammonium iodide (50 mg) in dry DMF (50 mL) at 25° C. (Step 36). The mixture was stirred for 1 hr at 65° C., poured over ice and then extracted with ether (2×50 mL). The combined ether extract was ##STR9## washed with water (3×50 mL), dried (MgSO4) and solvent was removed. Chromatography on silica gel using 10:90 ethyl acetate/hexane (Rf=0.39) afforded 8.9 g (70%) of the benzyl ether 40. 1H NMR (CDCl3) δ 1.6-1.9 (m, 8H, ring-CH2), 3.6 (m, 1H, CH--O), 4.0 (2, 4H, ketal--CH2), 4.6 (s, 2H, CH2 --O).

Provenance & Evidence