Hydrochloric Acid → HCID 68936252, compound

Participants

Reaction Steps

To a suspension of Example 19G (1.05 g, 1.43 mmol)) in ethanol (8 mL) was added concentrated HCl (104 μL, 1.28 mmol) in ethanol (2 mL), and the reaction mixture was stirred at room temperature for 3 hours. The reaction was poured into 1M NaHCO3 (35 mL) and extracted with tert-butyl methyl ether ( 3×35 mL). The combined organics were washed with brine (35 mL), dried over Na2SO4 and concentrated in vacuo to an oil. The crude material was purified by silica gel chromatography (5% ethyl acetate/hexane) then dried in vacuo at room temperature for one week to afford the titled compound (0.74 g, 83%) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 1.01 (s, 9 H) 1.02 (s, 9 H) 1.60-1.85 (m, 4 H) 2.46 (s, 1 H) 3.96-4.06 (m, 1 H) 4.63 (dd, J=6.79, 4.05 Hz, 1 H) 4.74 (t, J=5.35 Hz, 1 H) 4.85 (s, 1 H) 4.91 (s, 1 H) 7.27-7.45 (m, 12 H) 7.56-7.67 (m, 8 H); 13C NMR (100 MHz, CDCl3) δ 19.5, 19.6, 27.2, 27.3, 44.6, 67.0, 70.4, 107.9, 127.21, 127.24, 127.3, 129.33, 129.35, 129.5, 132.6, 133.2, 133.4, 133.9, 135.44, 135.48, 135.54, 135.6, 149.9; HRMS (ESI) [MNa+] calcd for C39H48O3Si2 643.3034, found 643.3022; Anal. calcd for C39H48O3Si2: C 75.43, H 7.79. Found: C 75.50, H 7.97.

Provenance & Evidence