Water → HCID 86663286, compound

Participants

Reaction Steps

To a stirred solution of 3-oxo-5-(triethylsilyloxy)-4,4-bis((triethylsilyloxy)methyl)pentanenitrile (1 equivalent) in anhydrous THF at 0° C. is added tetrabutylammonium fluoride (1-5 equivalents) then stirring is continued at rt until the reaction is substantially complete as monitored by LCMS or TLC. Water is added followed by extraction with EtOAc. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford 5-hydroxy-4,4-bis(hydroxymethyl)-3-oxopentanenitrile.

Provenance & Evidence