Diiodomethane → Methyl 3-(cyclopropylmethyl)-4,5-dimethoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To stirred dichloromethane (10 mL) at 0° C. was added Et2Zn (1.0 M in hexane, 10.0 mL, 10 mmol, 2 eq.). The resulting solution was then treated with a solution of TFA (0.77 mL, 10 mmol) in CH2Cl2 (5.0 mL) added over the course of 3 min. After stirring for 20 min at 0° C. diiodomethane (0.80 mL, 10.0 mmol) in CH2Cl2 was added. After 20 min at 0° C., a solution of 3-allyl-4,5-dimethoxybenzoic acid methyl ester (Example 30, Step 1, 1.18 g, 5.0 mmol) in CH2Cl2 (5.0 mL) was added and the reaction was warmed to 23° C. After 50 min the reaction was quenched by addition of 0.1 N HCl (25 mL) and then diluted with hexanes (100 mL). The organic layer was separated, washed with saturated NaHCO3 (100 mL), H2O (100 mL), brine (100 mL) dried MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel using 20% EtOAc in hexanes as an eluent to furnish 3-cyclopropylmethyl-4,5-dimethoxybenzoic acid methyl ester (0.96 g, 80% yield).

Provenance & Evidence