Potassium Carbonate → HCID 57523004, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of epoxy alcohol 12 (1.4 g, 4 mmol) in DMSO (5 mL) in a round-bottomed flask was added IBX (1.68 g, 6 mmol) in one portion and the reaction mixture was stirred for 1 h at ambient temperature (25° C.). The reaction mixture was quenched with diethylether (5 mL), H2O (0.5 mL) and filtered through a pad of celite. The residue was repeatedly washed with diethyl ether (50 mL). The filtrate was washed with H2O, brine, dried (Na2SO4) and concentrated to give the crude aldehyde, which was pure enough and used in the next step without further purification. To a solution of crude aldehyde and K2CO3 (900 mg, 8 mmol) in 20 mL dry MeOH and diethyl-1-diazo-2-oxopropylphosphonate (1.26 g, 6 mmol) were added under continuous stirring till completion of the reaction was indicated by TLC (2 h) (25° C.). The reaction mixture was diluted with diethylether (100 mL), washed with aq. solution of NaHCO3 and dried over Na2SO4. Evaporation of solvent yielded analytically pure terminal alkyne 13

Provenance & Evidence