Carbonochloridate → HCID 68828269, compound

Participants

Reaction Steps

To a solution of 430 mg (1.59 mmol) of 9 in anhydrous 1,2-dichloroethane (15 mL) at reflux was added 250 mg (1.75 mmol) of 1-chloethyl chloroformate drop wise. The resulting solution was heated under reflux for 20 h and then cooled to room temperature. The mixture was washed with saturated sodium bicarbonate solution, water, the organic layer evaporated, and the resulting oil dissolved immediately in methanol and refluxed overnight. After cooling to room temperature, the methanol was removed under reduced pressure, and the residue was treated with saturated sodium bicarbonate solution. The mixture was extracted with 3:1, methylene chloride/THF, and the combined organic extracts were washed once with water. Removal of a solvent provided 0.36 g (89%) of crude 10 as yellow oil: 1H NMR (300 MHz, CDCl3) δ 1.04 [s, 3H], 2.45-1.43 [m, 13H], 3.06 [m, 2H], 3.80 [s, 3H], 6.76 [m, 1H], 6.98 [m, 3H]; 13CNMR (300 MHz, CDCl3) δ 159.0, 128.3, 122.2, 116.9, 110.0, 55.6, 55.5, 43.8, 43.5, 36.4, 35.3, 30.7, 24.4, 22.4, 21.9

Provenance & Evidence