(3E)-4-Methoxy-3-buten-2-one → HCID 178495555, compound

Participants

Reaction Steps

LiHMDS (1M in THF, 845 mmol) was added dropwise to a solution of trans-4-methoxy-3-buten-2-one [51731-17-0] (845 mmol) in THF (2 L) at −78° C. After stirring for 15 min, a solution of 1-methyl-cyclopropanecarbonyl chloride [16480-05-0] (407 mmol) in THF (100 mL) was added. The resulting mixture was allowed to warm to rt over 2.5 h and then quenched by addition of a saturated solution of NH4Cl. The mixture was extracted with Et2O (2×). The combined organic phases were successively washed with a saturated solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a yellow solid. ESI-MS: [M+H]+ 183; TLC: Rf=0.29 (9:1 Hex/EtOAc).

Provenance & Evidence