Water → HCID 59487509, compound

Participants

Reaction Steps

A stirred solution of N-[2-(azidomethyl)-3,3,3-trifluoro-2-hydroxypropyl]-2,6-dichlorobenzamide (0.06 g) in dry tetrahydrofuran (30 ml) was treated with polymer bound triphenylphosphine (3 mmol/g, 2.01 g). The mixture was vigorously stirred at room temperature for 19 hours before water (3 ml) was added. Stirring was continued at room temperature for a further 24 hours. The suspension was then diluted with tetrahydrofuran (50 ml) and then filtered through a pad of hyflo. The pad was washed with further tetrahydrofuran (2×30 ml). The combined filtrate and washings were partitioned between ethyl acetate (100 ml) and water (50 ml). The separated organic phase was further washed with water (2×50 ml), passed through a hydrophobic frit and concentrated in vacuo and then re-evaporated in vacuo with ethanol (1×20 ml) to give the title compound (0.84 g) as a near colourless gum.

Provenance & Evidence