Hydrochloric Acid → HCID 53963642, compound

Participants

Reaction Steps

670 mg of the above (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-(fluoromethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester were dissolved in tetrahydrofuran followed by addition of 2N aqueous hydrochloric acid and stirring for 2 hours at room temperature. The reaction mixture was neutralized after adding water, and then extracted with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a pale yellow oil from the hexane-ether eluate in the form of (4aS,7aR)-7-(fluoromethyl)-1-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester (500 mg, yield: 98%). The physicochemical properties of this compound are described below.

Provenance & Evidence