Iodoethane → HCID 59226841, compound

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (8 mg, 0.058 mmol) was added to a solution of intermediate 2-(4-hydroxy-benzyl)-4-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-hydroxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-benzonitrile (see example 6; 8.9 mg, 0.022 mmol) in acetone (0.4 mL), followed by iodoethane (4 microL, 0.044 mmol) at room temperature. The mixture was stirred at 45° C. overnight. The mixture was diluted with ethyl acetate (60 mL) and washed with water. The organic layer was dried over sodium sulfate and evaporated to dryness. Purification by preparative Thin Layer Chromatography over silica gel (eluting with methanol in dichloromethane: 1 to 9 in volume) allowed isolation of desired product 7A (2.4 mg; 26% yield).

Provenance & Evidence