Oxalyl chloride → HCID 86611022, compound

Participants

Reaction Steps

To a solution of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(1-hydroxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (1.50 g) in dichloromethane (7 mL) cooled in an ice-bath is added oxalyl chloride (1 mL). The solution is stirred at ambient temperature for 4 h and then concentrated under reduced pressure. The residue is dissolved in dry tetrahydrofuran (4 mL), cooled in an ice-bath and treated with sodium borohydride (86 mg). The resultant mixture is stirred at room temperature for 16 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4), the solvent is removed in vacuo and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1).

Provenance & Evidence