Water → HCID 86663282, compound

Participants

Reaction Steps

To a stirred solution of 5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-4-methyl-3-oxopentanenitrile (1 equivalent) in anhydrous THF at 0° C. is added tetrabutylammonium fluoride (1-5 equivalents) and stirring is continued at rt until the reaction is substantially complete as determined by LCMS or TLC. Water is added followed by extraction with EtOAc. The extracts 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-(hydroxymethyl)-4-methyl-3-oxopentanenitrile.

Provenance & Evidence