Dimethyl Sulfate → HCID 86747857, compound

Participants

Reaction Steps

To a suspension of 3.60 g (90 mmol, 2 equiv) of 60% NaH in mineral oil, washed three times with pentane, in 170 mL of tetrahydrofuran at room temperature under argon was added a solution of 10.00 g (45 mmol) of E,E-farnesol in 30 mL of tetrahydrofuran, and the resulting mixture was heated at reflux for 0.5 hours. After having cooled to room temperature the reaction was treated with 1.66 g (4.5 mmol, 10%) of tetra-n-butylammonium iodide and 5.50 g (47.5 mmol, 1.05 eq.) of the sodium chloroacetate, and heated to reflux for 20 hours. The mixture was cooled to 0° C. and 200 mL of dimethylformamide was slowly added, followed by 9.4 mL (99 mmol, 2.2 eq.) of dimethylsulfate. After four hours, the reaction was diluted with 600 mL of 1:1 diethyl ether:hexane, washed with five 100 mL portions of H2O and 100 mL of brine, dried over MgSO4, and evaporated to afford 14.09 g of a dark yellow oil. Purification by flash chromatography on 1000 g of Merck 9385 silica, eluted with 5:95 ethyl acetate:hexane provided 10.19 g (77%) of title ester as a yellow oil.

Provenance & Evidence