Acetic Acid → HCID 86752988, compound

Participants

Reaction Steps

To a solution of cis and trans 4-(t-butyldiphenylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-oxathiolane (example 42) (5.00 g, 10.07 mmol) in tetrahydrofurane (300 mL) was added tetrabutylammonium fluoride (15.0 mL, 15.0 mmol, 1.5 eq) at room temperature. The solution was stirred at room temperature for 45 min and acetic acid was added (850 μL) followed by evaporation under reduced pressure. The crude material was purified by flash chromatography with ethyl acetate to give the pure compound (2.47 g) in 96% yield. 1H NMR (300 MHz, CDCl3) δ: 1.36 (2t, 6H, J=7.1 Hz, CH3), 3.20 (m, 0.33H, CHAHBO for cis), 3.64 (m, 1.33H, CH2O for trans), 3.75 (m, 1H, OH and 0.33H, CHAHBO for cis), 3.95 (dd, 0.33H, J=6.1 Hz, 9.9 Hz, CHAHBO for cis), 4.23 (m, 4H, CH2 ; 1H H-4; 0.66H, CHAHBO for trans), 4.33 (dd, 0.66H, J=7.6 Hz, 9.9 Hz, CHAHBO for trans), 4.49 (dd, 0.33H, J=3.5 Hz, 9.9 Hz, CHAHBO for cis), 5.23 (d, 0.33H, 2JHP =9.9 Hz, H-2 for cis), 5.33 (d, 0.66H, 2JHP =9.3 Hz, H-2 for trans).

Provenance & Evidence