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TCI Practical Example: Deoxygenative Fluorination of an Alcohol Using PyFluor
We are proud to present the deoxygenative fluorination of the hydroxy group of 2,3-O-isopropylidene-D-ribonolactone using PyFluor as a fluorinating agent.
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Used Chemicals
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Procedure
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A solution of PyFluor (513 mg, 3.19 mmol) in dry toluene (3.6 mL) was added to a solution of 2,3-O-isopropylidene-D-ribonic γ-lactone (500 mg, 2.66 mmol) and DBU (0.79 mL, 5.31 mmol) in toluene (3.0 mL) at 0 °C and the solution was stirred at room temperature for one day. The reaction mixture was quenched with water (10 mL) and the aqueous layer was extracted with ethyl acetate (3 x 5 mL). The combined organic layer was washed with sat. NH4Cl aq. and brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 - 15:85 on silica gel) to give the fluorinated compound 1 as a white solid (309 mg, 61% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:2, Rf = 0.33).
It was easier to weigh after melting PyFluor by heating with hot water bath because melting point of PyFluor is 26 °C.
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Analytical Data
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Fluorinated Compound 1
1H NMR (270 MHz, DMSO-d6); δ 4.94-4.74 (m, 4H), 4.64 (ddd, J = 3.0, 10.8, 27.8 Hz, 1H), 1.37 (s, 3H), 1.33 (s, 3H).
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Lead Reference
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- PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent