Water → HCID 22592416, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium hydride (247 mg, 6.16 mmol) in dry THF (6 ml) at 0° C. under nitrogen was added a solution of diethylcyanomethyl phosphonate (0.98 ml, 6.16 mmol) in 2 ml THF and the whole stirred at 0° C. for 1 h. 5-Acetyl-2,3-dihydro[b]benzofuran (Aldrich) (1 g, 6.16 mmol) in THF (2 ml) was added dropwise and the whole stirred at room temperature for 16 h. Water (20 ml) and EtOAc (20 ml) were added, the organic layer separated, and the aqueous layer extracted with EtOAc (2×20 ml). The combined organics were dried over MgSO4, filtered and evaporated to afford a pale brown oil which solidified on standing. This solid was purified by column chromatography using 20-30% EtOAc in pentane as eluant to give the title product (789 mg, 69%); 1HNMR (400 MHz, CDCl3) δ: 2.4 (s, 3H), 3.2 (t, 2H), 4.6 (t, 2H), 5.5 (s, 1H), 6.7 (d, 1H), 7.2 (d, 1H), 7.3 (s, 1H); LRMS: M+NH4 203 (ES+).

Provenance & Evidence