Tetrabutylammonium Fluoride → HCID 86714071, compound

Participants

Reaction Steps

Step 4) To a solution of compound 149 (870 mg, 0.98 mmol) in tetrahydrofuran (10.0 mL) was slowly added tetrabutylammonium fluoride solution (5.0 mL, 1.0M in tetrahydrofuran) at 0° C. and the reaction mixture was stirred for 2 h. The resulting mixture was quenched with sat. NH4Cl solution, diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((4-ethylphenyl)(hydroxy)methyl)-4-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (150, 500 mg, 89%) as a pale yellow solid.

Provenance & Evidence