5-Methyl-2-thiophenecarboxaldehyde → HCID 23577305, compound

Participants

Reaction Steps

To a solution of tert-butyl diethylphosphonoacetate (1.12 mL, 4.76 mmol) in THF (5 mL) at −78° C. was added LHMDS (1.0M in THF, 4.76 mL, 4.76 mmol). After 5 min at −78° C. 5-methyl-2-thiophene-carboxaldehyde (0.43 mL, 3.96 mmol) was added. The reaction mixture was warmed to RT, stirred for 10 min and poured onto EtOAc/H2O. The layers were separated and the organic layer was washed with H2O, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica (gradient elution; hexanes to 4:1 hexanes:EtOAc) to give tert-butyl (2E)-3-(5-methylthien-2-yl)prop-2-enoate as a clear oil.

Provenance & Evidence