Pyridine → HCID 57450872, compound

Participants

Reaction Steps

A solution of indenol 9 (100.5 g, 0.56 mmol), 6 mL of acetic anhydride and 5 mL of pyridine was stirred for 16 hr at rt. The reaction mixture was diluted with ether (80 mL), washed with 10% HCl (50 mL×4), saturated aqueous NaHCO3, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by chromatography (5% EtOAc/hexane) gave 112.8 mg (91%) of compound 10 as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.20 (br d, J=2.4 Hz, IH), 5.08 (qt, J=7.2, 2.0 Hz, 1H), 2.33 (m, 2H), 2.18 (m,1H), 1.80 (m, 2H) 2.04 (s, 3H), 1.65 (dt, J=7.2, 2.4 Hz, 3H), 1.55 (m, 6H),1.08 (s, 3H); MS, m/z (70 eV, EI) 343 (M-tert-Bu+, 100%); HRMS Calcd. 343.1761 for C20H40O4 Si2 -tert-Bu+, found 313.1108.

Provenance & Evidence