1-Chloro-3-methyl-2-butene → HCID 22603010, compound

Participants

Reaction Steps

In a 500-mL round-bottom flask, a mixture of methyl 5-(4-methoxy-2,6-dimethylbenzyl)-2-furoate (202) and methyl 5-(2-methoxy-4,6-dimethylbenzyl)-2-furoate (203) (4.52 g, 17.38 mmol) and anhydrous DMSO (50 mL) were placed. To this solution, 1-chloro-3-methylbut-2-ene (1.91 g, 18.25 mmol) and potassium tert-butoxide (2.25 g, 20.07 mmol) were added. The reaction mixture was placed under nitrogen and stirred at room temperature for 3 hours. The reaction mixture was poured into, water and extracted with ethyl acetate. The separated organic layer-was washed with water (2×) and brine and dried over MgSO4 then concentrated to yield a mixture of methyl 5-{2,6-dimethyl-4-[(3-methylbut-3-enyl)oxy]benzyl}-2-furoate (204) and methyl 5-{2,4-dimethyl-6-[(4-methylpent-4-enyl)oxy]benzyl}-2-furoate (205) (3.64 g, 64% yield).

Provenance & Evidence