Ethyl diazoacetate → HCID 67360452, compound

Participants

Reaction Conditions

Reaction Steps

Compound H6.6 (50.0 mg, 211 μmol) and rhodium (ii) acetate, dimer (9.31 mg, 21.1 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) were mixed in 1.6 mL dry DCM. The resulting solution was refluxed at 45° C. for 10 minutes. Ethyl diazoacetate (26.2 μL, 253 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) was then added to the mixture very slowly. After 1 hour, the reaction was cooled to room temperature. The catalyst was then filtered off, and the solvent was concentrated down with silica gel. The product was purified by column chromatography to give H6.7 (25.1 mg, 36.9%). NMR confirmed that the product was the trans isomer. MS ESI (pos.) m/e: 324.2 (M+H)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.55-7.60 (3H, m), 7.37-7.47 (4H, m), 4.90 (2H, d, J=3.7 Hz), 4.12 (2H, q, J=7.1 Hz), 2.92 (2H, d, J=19.3 Hz), 2.82 (1H, dd, J=8.6, 6.4 Hz), 2.31 (1H, dd, J=8.4, 5.0 Hz), 2.19 (2H, ddd, J=8.7, 6.8, 2.8 Hz), 1.36 (1H, dd, J=6.0, 5.5 Hz), 1.21 (3H, t, J=7.1 Hz).

Provenance & Evidence