Tetrahydrofuran → HCID 86718364, compound

Participants

Reaction Steps

To a solution of ethyl 2-triethylphosphono-acetate (2.2 mL, 11 mmol) in THF (30 mL) at 0° C. was added KOtBu (1.01 g, 9.02 mmol) and stirred for 1 hour at room temperature. The mixture was cooled to −78° C. To the mixture was added slowly a solution of 2.12a (0.993 g, 3.92 mmol) in THF (10 mL. The reaction mixture was poured onto a mixture of ice-cold water/Et2O (10 mL/600 mL), washed with brine twice, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-50%, EtOAc/heptane) to give 2.12b (1.14 g, 90% yield). MS m/z (M+23) 346.2. 1H NMR (E, major isomer) (400 MHz, CDCl3) δ ppm 1.05 (d, J=6.90 Hz, 2H) 1.07-1.18 (m, 1H) 1.19-1.32 (m, 2H) 1.36-1.46 (m, 2H) 1.44 (s, 4H) 1.55-1.57 (m, 1H) 4.14-4.22 (m, 1H) 5.74-5.85 (m, 1H) 6.14-6.19 (m, 1H) 6.27-6.33 (m, 1H) 6.86 (dd, J=15.70, 8.17 Hz, 1H) 7.26 (s, 1H) 7.31-7.37 (m, 1H).

Provenance & Evidence