Methyl iodide → 1,1-Dimethylethyl cyclopropyl({2,3-dichloro-5-[2-(methyloxy)ethyl]phenyl}methyl)carbamate

Participants

Reaction Steps

1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-hydroxyethyl)phenyl]-methyl}carbamate (1 eq.) was taken up in THF (0.3 M). To this solution was then added sodium hydride (60% w/w dispersion in oil, 1 eq.) and the resulting suspension was stirred at RT for 5 min. Finally, iodomethane (10 eq.) was added and the now pale yellow solution was stirred in darkness at RT for another 10 h. The volatiles were then removed in vacuo and the resulting residue partitioned between ether and 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to give the title compound (contaminated with oil) as a pale yellow oil.

Provenance & Evidence