Propargyl alcohol → HCID 54086541, compound

Participants

Reaction Steps

Bis (triphenylphosphine)palladium dichloride (17.0 mg, 0.02 mmol) and cuprous iodide (2.0 mg, 0.01 mmol) are added to a suspension of methylene bis (p-bromobenzoate) (0.500 g, 1.21 mmol) prepared as described in Example 14 and propargyl alcohol (0.16 ml, 2.66 mmol) in triethylamine (10 ml) with good stirring, at 20° C., under a dry N2 atmosphere. After 10 days at 20° C., the triethylamine is removed under reduced pressure, water (20 ml) is added and the mixture is extracted with dichloromethane (3×15 ml). The dichloromethane phases are washed with hydrochloric acid (0.5M, 10 ml), dried (MgSO4) and the dichloromethane removed under reduced pressure to give 0.37 g (85%) of the crude product. 1H NMR (60 MHz, CDCl3): δ 3.67 (2H, s, OH), 4.47 (4H, s, CH2 --O), 6.18 (2H, s, O--CH2 --O), 7.2-7.5 (4H, Ar), 7.8-8.0 (4H, Ar).

Provenance & Evidence