Potassium Carbonate → HCID 59745015, compound

Participants

Reaction Steps

Dimethyl-2-oxopropylphosphonate (1.2 equiv, 1.5 g, 9.1 mmol) was added to a suspension of K2CO3 (3 equiv, 3.1 g, 23 mmol) and p-TsN3 (1.2 equiv, 1.8 g, 9.1 mmol) in MeCN (144 mL). The mixture was then stirred for 2 h. A solution of the methyl 2-(4-(3-oxopropyl)phenyl)acetate (1 equiv, 1.56 g, 7.6 mmol) in MeOH was then added in one portion and the reaction was stirred overnight. The solvent was evaporated under reduced pressure. The residue was partitioned between Et2O (100 mL) and water (100 mL). The aqueous phase was separated and extracted with Et2O (25 mL) twice. The organic phases were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column eluting with 0-30% EtOAc in hexanes to afford methyl 2-(4-(but-3-ynyl)phenyl)acetate in 980 mg (64%). LRMS: 202.5 (calc) 225.1 (found)(MNa)+.

Provenance & Evidence