HCID 67019287, compound → HCID 67019292, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isobutyl ether 8 (88.0 g, 370 mmol) in anhydrous ether (250 mL) was cooled to 0° C. in an ice bath and treated dropwise with ethyl lithium (650 mL). The resulting mixture was stirred at 0° C. for 2 hours and then at room temperature for 48 hours. The reaction mixture was slowly quenched with water (200 mL) and extracted with ether (2×200 mL). The combined organic layer was dried (Na2SO4) and concentrated under vacuum to provide 75 g of crude oil, which was purified by chromatography (silica gel; hexane/ether 4:1) to give 58.0 g (80.1%) of 9 as an oil: MS m/z 195 (M+1); 1H NMR (300 MHz, CDCl3) δ 2.4-2.3 (m, 4H), 2.3-2.2 (m, 4H), 1.95-1.85 (m, 2H), 1.6-1.5 (m, 1H), 1.2-1.1 (m, 2H), 1.1 (t, 3H), 0.9 (d, 6H); 13C NMR (CDCl3) δ 199.2, 159.9, 135.4, 39.0, 38.1, 30.0, 28.5, 27.8, 22.9, 22.6, 22.5, 12.4.

Provenance & Evidence