Tetrahydrofuran → HCID 68069072, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottom flask equipped with a magnetic stir bar was added t-BuOK (352 mg, 3.14 mmol) and THF (5 mL). The solution was cooled to 0° C. Triethylphosphonoacetate (0.576 mL, 2.88 mmol) was added slowly by syringe pump over 30 min. Using 13 (500 mg, 2.62 mmol) in THF (5 mL), the aldehyde was added via syringe pump over 30 min at 0° C. When the addition was complete, the reaction was warmed to room temperature and stirred for 2 h. The reaction was quenched with sat aqueous NH4Cl (10 mL) and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography using a gradient of 25-50% EtOAc in hexanes. The appropriate fractions were combined and concentrated in vacuo to give the title compound as a white solid (631 mg, 92% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (t, J=7.20 Hz, 3H) 1.43 (d, J=6.82 Hz, 3H) 4.18 (q, J=7.16 Hz, 2H) 4.70-4.77 (m, 1H) 6.38 (d, J=15.92 Hz, 1H) 7.13 (d, J=2.02 Hz, 1H) 7.33 (dd, J=8.72, 2.15 Hz, 1H) 7.56 (d, J=15.92 Hz, 1H) 10.78 (s, 1H). ESI-MS: m/z 262.2 (M+H)+.

Provenance & Evidence