HCID 59745010, compound → HCID 59744997, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of PhMgBr (1 equiv, 0.45 mmol) was added dropwise to a solution of methyl 2-(3-(4-oxobutyl)phenyl)acetate (1 equiv, 100 mg, 0.45 mmol) in THF (2 mL) at 0° C. The reaction was then allowed to warm to 23° C. over 1 h. The reaction was quenched by the addition on sat. aq. NH4Cl (10 mL). The aqueous phase was separated and extracted with EtOAc (2×5 mL). The organic layers were then combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 0-50% EtOAc in hexanes to afford methyl 2-(3-(4-hydroxy-4-phenylbutyl)phenyl)acetate in 78 mg (58%) as a clear translucent oil. LRMS: 298.4 (calc) 321.2 (found)(MH)+.

Provenance & Evidence