1,4-Dioxaspiro[4.5]decan-8-one → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,4-dioxaspiro[4.5]decan-8-one (3.00 g, 19.2 mmol) in THF (80 mL) was dropwise added (4-fluorophenyl) magnesium bromide (1.0 M in THF, 28.8 mL, 28.8 mmol) at 0° C. over 15 min. The mixture was stirred at 0° C. for 30 min, and then quenched with aqueous NH4Cl (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (30 mL). The combined organic layers were washed with brine (15 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 80:20 hexane/EtOAc to 50:50 hexane/EtOAc) to give title compound (1.96 g, 40%) as a colorless solid:

Provenance & Evidence