Sodium hydride → HCID 86759887, compound

Participants

Reaction Conditions

Reaction Steps

A 60% suspension of NaH (2.1 g, 53.7 mmol) is added to a solution of 3-[3-(3-hydroxyprop-1-ynyl)phenyl]prop-2-yn-1-ol (A5, 0.5 g, 2.68 mmol) in absolute THF (20 ml), and the mixture is stirred at 70° C. for 2 h. After cooling to RT, methyl bromoacetate (5.2 ml, 53.7 mmol) is added dropwise to the reaction solution, and the mixture is stirred at RT overnight. For work-up, the reaction solution is poured into an ice-cooled semisaturated aqueous NH4Cl solution (25 ml) and extracted (2×) with ethyl acetate. The combined organic phases are dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [Tol/Ac (9:1)] over a silica gel column gives the title compound (0.85 g) as a colorless residue. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.80.

Provenance & Evidence