Iodoethane → HCID 66875058, compound

Participants

Reaction Steps

To a stirred solution of Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate (Step B, 4.84 g, 16.2 mmol) in dry THF (60 ml) and HMPA (15 ml) at −78° C. under a dry argon atmosphere was added LDA drop wise (2 M solution in THF, 25 ml, 48.72 mmol), and the resulting orange solution was stirred at low temperature for 30 minutes before CH3CH2I (10.13 g, 64.96 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for 15 hours. The reaction was quenched with aqueous citric acid, and the product was extracted with EtOAc (2×), the organic phase washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound.

Provenance & Evidence