Tetrahydrofuran → HCID 67404601, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask, 3.2054 g (10.2330 mmol, 1.0 eq) of the protected alcohol was dissolved in 83 mL of reagent-grade THF under N2 atmosphere. The solution was then cooled to −78° C. using a dry ice/acetone bath. 4.50 mL (11.2563 mmol, 1.1 eq) of the n-BuLi (2.5 M in hexanes) was added dropwise to the solution. The reaction was allowed to stir for 30 min while maintaining lowered temperature. 3.54 mL (15.3495 mmol, 1.5 eq) of the triisopropyl borate was added to the reaction slowly at −78° C. Upon complete addition of the triisopropyl borate, the reaction was allowed to gradually warm to room temperature overnight, maintaining inert atmosphere. The following morning, the reaction was quenched by the slow addition of 20 mL of 6M HCl (aq). The reaction was allowed to stir for 1 h. The reaction solution was then diluted with 50 mL of EtOAc and poured into 50 mL of H2O. The layers were separated, and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined, washed with brine, and dried over Na2SO4. The solution was decanted and the solvent was removed under reduced pressure. The oily material was then taken up in 25 mL of DCM and stirred together with 25 mL of 10% NaOH solution. The layers were separated and the aqueous layer was neutralized with 2N HCl. The aqueous layer was then re-extracted with EtOAc (3×30 mL) and the organic layer was washed with brine (1×50 mL) and dried over Na2SO4. The solvent was then removed under reduced pressure, yielding a colorless oil. LCMS (m/e): 177 (M+H); 1H NMR (400 MHz, acetone-d6) δ ppm 1.22-1.28 (m, 3H) 3.82-3.92 (m, 1H) 4.14 (dd, J=10.84, 3.95 Hz, 1H) 7.15-7.31 (m, 2H) 7.35-7.48 (m, 1H) 7.75 (d, J=7.17 Hz, 1H).

Provenance & Evidence