Hydrochloric Acid → (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

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Reaction Steps

A solution of (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (24 mg, 0.06 mmol) in methanol (1 mL) was treated with 2N HCl (0.36 mL, 0.18 mmol) and the resulting solution was heated at reflux for 20 minutes. After cooling, the mixture was concentrated under vacuum to a residue that was dissolved in EtOAc (60 mL) and washed with 5% NaHCO3 (30 mL). The aqueous phase was back-extracted with EtOAc (30 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by PLC, using 1:1 hexanes-EtOAc as developing solvent, to afford (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

Provenance & Evidence