Acetate → HCID 50942718, compound

Participants

Reaction Steps

To a stirred solution of the above acetate (54 mg, 0.32 mmol) and 2,6-lutidine (74 μL, 0.63 mmol) in CH2Cl2 (1 mL) was added tert-butyldimethylsilyltrifluoromethanesulfonate (125 mg, 108 μL) at −78° C. under argon. The mixture was stirred for 10 min at which point reaction completion was observed. Sat. aq. NaHCO3 solution (1 mL) and additional CH2Cl2 (2 mL) were added. The two layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×2 mL). The combined organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel using hexanes/EtOAc (20:1) as the eluent to afford silylated product 5 (90 mg, >99%) as a colorless oil. TLC: Rf=0.68 (hexanes/EtOAc=3:1); 1H NMR (CDCl3, 300 MHz) δ 5.68 (s, 2H), 4.45 (dt, J=5.1, 6.3 Hz, 1H), 4.14 (t, J=6.9 Hz, 2H), 2.67-2.55 (m, 1H), 2.47 (dd, J=6.9, 15.4 Hz, 1H), 2.23 (dd, J=4.8, 15.4 Hz, 1H), 2.04 (s, 3H), 2.01-1.85 (m, 1H), 1.72-1.56 (m, 1H), 0.88 (s, 9H), 0.06 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 171.2, 132.7, 128.4, 73.6, 63.8, 45.9, 41.0, 27.4, 25.8, 21.0, 18.1, −4.6, −5.0.

Provenance & Evidence