Water → Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylate

Participants

Reaction Steps

To trimethylsulfoxonium iodide (32 g, 1.2 equiv) in DMSO (250 ml) was added ground KOt-Bu (17.62 g, 1.3 equiv) and this mixture was stirred at r.t. for 30 min. A solution of the styrene 17 (28.53 g, 121 mmol) in DMSO (55 ml) was then added and this mixture was stirred at r.t. for 3 h. The reaction was poured into water (1.0 L) mixed with sat. NHCl (350 ml). The product was extracted into hexane (2×300 ml) and this solution was washed with water and brine, dried over Na2SO4 and filtered through silica (400 ml). The product was then eluted with EtOAc/hexane 15 and 20% to yield 18 (21.1 g, 70%) as a colorless oil.

Provenance & Evidence