Potassium Phosphate, Tribasic → 1,1-Dimethylethyl cyclopropyl({2-methyl-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl[(5-chloro-2-methylphenyl)methyl]cyclopropylcarbamate (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1 eq.) were combined in n-BuOH (0.48 M). To this solution was then added tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.02 eq.), [2′,6′-bis(methyloxy)-2-biphenylyl](dicyclohexyl)phosphane (0.08 eq.) and powdered potassium phosphate (2 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen before the resulting suspension was heated at 100° C. for 16 h. The now black suspension was cooled to RT, diluted with EtOAc and filtered through a pad of SiO2. The filtrate was then concentrated in vacuo and the crude product thus obtained was directly subjected to purification by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc). The title compound was isolated as a pale yellow oil.

Provenance & Evidence