Perfluoropentanoic acid → HCID 86759615, compound

Participants

Reaction Steps

A solution of (2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (“hydroxymethyl EDOT”, 1.20 g, 6.97 mmol) in dichloromethane (30 mL) was chilled to 0° C. under argon. Neat 2,2,3,3,4,4,5,5,5-nonafluoropentanoic acid (1.93 g, 7.35 mmol) was added by pipette. Quickly 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (2.30 g, 7.80 mmol) and 3,4-dimethylaminopyridine (0.1 g, 0.82 mmol) were added and the solution was allowed to come to room temperature overnight. The solvent was evaporated at <30° C. and the residue purified by repeated column chromatography on silica gel using a gradient elution starting with 3:1 hexane/dichloromethane and ending with 1:1 hexane/dichloromethane. The product (2.10 g, 5.02 mmol) was a colorless oil that solidifies at −20° C. (Formula (4), left-hand side). Overall product yield was 53%.

Provenance & Evidence