Sodium hydride → Ethyl trans-2-phenylcyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of NaH (40.7 g) in DMSO (2.5 L) under N2 was added portion wise trimethyl sulfoxonium iodide (396 g, 1.80 mol, 1.76 equiv). A solution of 31 (180 g, 1.02 mol, 1.00 equiv) in 1:1 DMSO/THF (2 L) was added, and the reaction mixture was stirred at 25° C. overnight. The reaction mixture was quenched with 1N HCl (1 L) and extracted with EtOAc (2×2 L). The combined organic layers were washed with water (2×2 L) and brine (1×2 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (5 to 12.5% EtOAc) to afford 153 g (79%) of trans-ethyl-2-phenylcyclopropane-1-carboxylate (33) as a light yellow oil.

Provenance & Evidence