Methyl iodide → 6-Bromo-2,5,7-trimethyl-1-oxo-indan-2-carboxylic acid ethyl ester

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Reaction Steps

To the stirred solution of compound 4 (5.0 g, 16.1 mmol) in dry THF (50 mL), A 60% dispersion of sodium hydride (0.85 g, 35.4 mmol) in solid addition funnel was added portion wise at 0° C. The reaction mixture was warmed to room temperature and stirred for another 1 h. Then MeI (2.0 mL, 32.15 mmol) was added dropwise at 0° C. under argon atmosphere. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution at 0° C. and allowed to stir for 15 min. Then crude reaction mixture was extracted with ethyl acetate (100 mL×2 mL), washed with water (100 mL), brine (100 mL) dried (Na2SO4) and concentrated in vacuo. Purification by silica gel column chromatography (hexanes/ethyl acetate, 15:1, v/v) gave pure compound 5 (4.5 g, 86.5%).

Provenance & Evidence