Tetrabutylammonium Fluoride → HCID 86595787, compound

Participants

Reaction Steps

(3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-{[tert-butyl(diphenyl)silyl]oxy}butyl)-1,3-thiazol-4-yl]butanoate 6.55 g, 10.39 mmol) was dissolved in THF (20 mL) and tetrabutyl ammonium fluoride (1M, 23.39 mL, 23.39 mmol) was added. The reaction was stirred at ambient temperature for 2 hours. Dilute with diethyl ether, and wash with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and purified via silica gel chromatography (eluent: 4:1 Hexane:Ethyl Acetate) to give the product as a colorless oil. Yield: 3.08g (76%) 1H NMR (DMSO-d6) δ6.95–6.92 (m, 1H), 6.85–6.83 (m, 1H), 6.75–6.71 (m, 1H), 6.63–6.59 (m, 1H), 5.94 (s, 2H), 3.95–3.85 (q, 2H), 3.46–3.38 (m, 3H), 2.98–2.85 (m, 4H), 2.68–2.51 (m, 2H), 1.75–1.65 (m, 2H), 1.50–1.41 (m, 2H), 1.08–1.02 (t, 3H).

Provenance & Evidence