Methyl iodide → HCID 67519647, compound

Participants

Reaction Steps

To a stirred solution of Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate (Step B, 4.53 g, 14.5 mmol) in dry THF (30 ml) at −68° C. under a dry argon atmosphere was added LiHMDS drop wise (1 M solution in THF, 21.77 ml, 21.77 mmol), and the resulting orange solution was stirred at low temperature for 30 minutes before CH3I (20.60 g, 145.2 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for 15 hours. The reaction was quenched with ice, and the product was extracted with EtOAc (2×), the organic phase was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ether 5:1) to give the title compound.

Provenance & Evidence