Methyl iodide → HCID 18009397, compound

Participants

Reaction Conditions

Reaction Steps

The compound from step B (1.03 g, 3.2 mmol) was dissolved in DME (40 ml) under argon and cooled to −20° C. and LDA (1.6 ml, 3.2 mmol) was added. The mixture was then warmed to room temperature and stirred for 30 min. Methyl iodide (0.2 ml, 3.2 mmol) was slowly added over 15 min. to give a cloudy suspension. The mixture was again cooled to −20 C. and a second portion of LDA (1.6 ml, 3.2 mmol) was added. After the mixture was warmed to room temperature and stirred for 30 min a second portion of methyl iodide (0.2 ml, 3.2 mmol) was added and the mixture stirred for 60 h. The mixture was added to cold NaHCO3 (100 ml) and extracted with ethyl acetate (3×100 ml). The organic layer was washed with 5% HCl (3×25 ml) then dried and evaporated. The residue was chromatographed on silica gel with hexane/ethyl acetate (2:1) to give 0.208 g (24%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 1.24 (6H, t, CH(CH3)2), 3.60 (1H, m, CH(CH3)2, 3.71 (3H, s, OCH3), 3.89 (3H, s, OCH3), 3.93 (3H, s, OCH3), 6.86-8.32 (6H, ArH).

Provenance & Evidence