2-Bromoethanol → HCID 21717715, compound

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Reaction Steps

To a solution of 5-(3,4-Dichloro-phenyl)-3-(3-[1,3]dioxolan-2-yl-phenyl)-1H-[1,2,4]triazole (mixture of tautomers) (400 mg, 0.31 mmol) in acetonitrile (5 ml) was added 2-bromoethanol (156 μl, 2.21 mmol) and BEMP on poystyrene resin support (2.3 mmol/g, 960 mg). This mixture was shaken at r.t. until the starting material had been consumed (5 d), then aminomethyl polystyrene (1.1 mmol/g, 147 mg) was added and the mixture shaken for a further 2 h at r.t. The mixture was then filtere, washed with acetonitrile and evaporated to afford an isomeric mixture of alkylated acetals which were chromatographically separated over SiO2 (Merck 230-400 Mesh) eluting with EiOAc/nHexane (1:4). The purified isomer was dissolved in THF (3 ml) and treated with 4N HCl (0.3 ml) at r.t. for 3 h, then the mixture was adjusted to pH 9 with NaHCO3, and the aqueous phase extracted twice with EtOAc. The organic phases were combined, dried, filtered and evaporated to afford the title aldehyde as a off white semi-solid (33 mg, 9% yield), MS: m/e=361 (M+H+). The position of alkylation on the triazole ring was assigned by 1H-NMR, nOe spectroscopy.

Provenance & Evidence