Pyridine, hydrofluoride (1:1) → {3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl-sulfanyl]propylsulfanyl}acetic Acid Methyl Ester

Participants

Reaction Steps

Hydrogen fluoride-pyridine (220 μL) was added to a solution of bis-TBDMS ether 7 (70 mg, 0.11 mmol) in CH3CN (2.0 mL) at 0° C. The reaction was warmed to room temperature, stirred 1 h, and recooled to 0° C. The reaction was quenched with saturated aqueous NaHCO3 until gas evolution ceased. The mixture was extracted with CH2Cl2 (4×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 100% CH2Cl2 followed by 30:1 CH2Cl2:MeOH) provided 40 mg (90%) of the above titled compound.

Provenance & Evidence