Methyl iodide → HCID 59363826, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamide (0.46 g, 4.56 mmol) in THF (10 ml) was added n-Butyl lithium (3 ml of 1.6 M, 4.80 mmol) drop wise at −78° C. in nitrogen atmosphere and stirred for 30 minutes, to this slowly added solution of (4-Methanesulfonyl-phenyl)-acetic acid methyl ester (1.0 g, 4.38 mmol) and 1,3 dimethyl 3,4,5,6-tetrahydro-2-pyrimidone (3.17 g, 27.75 mmol), stirred for 1 hour at −78° C., followed by drop wise addition of solution of iodomethane in THF (1.14 g, 8.03 mmol in 10 ml) and stirred at the same temperature for one hour. Reaction mixture was allowed to come at RT and stirred for overnight. The reaction mixture was then poured into water (40 ml) under stirring, THF was removed under reduced pressure, and residue was extracted with ethyl acetate (2×25 ml), organic layer was washed with water (2×20 ml), dried over sodium sulfate and solvent was removed under reduced pressure to get oily residue which was purified by column chromatography over silica gel (100-200 mesh), using 50% ethyl acetate in hexanes as an eluent to afford 2-(4-Methanesulfonyl-phenyl)-propionic acid methyl ester (0.94 g, 88.5%) as white solid. 1H NMR (400 MHz, CDCl3): δ 1.54 (d, J=7.2 Hz, 3H), 3.06 (s, 3H), 3.69 (s, 3H), 3.83 (q, J=7.2 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.90 (d, J=8.4 Hz, 2H), 2-Bromo-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (O1-III)

Provenance & Evidence