HCID 131727740, compound → HCID 131727739, compound

Participants

Reaction Steps

10% Cd/Pb couple (288 mg, 2.35 mmol, 20 eq) was added to a rapidly stirring mixture of 20 (154 mg, 0.12 mmol), THF (3 mL) and 1 N NH4OAc (3 mL). The reaction mixture was allowed to stir for 3 hours when TLC showed complete consumption of the starting material. The solids were filtered and rinsed with H2O and DCM. The aqueous layer was extracted with DCM (3×15 mL) and the organic extracts were combined, washed with brine (40 mL) and dried (MgSO4). Filtration and evaporation of solvent afforded the crude product which was purified by flash column chromatography (99:1 v/v CHCl3/MeOH then gradient to 98:2 v/v CHCl3/MeOH) to afford 21 as a yellow glass (59 mg, 72%): 1H NMR (400 MHz, CDCl3) δ 7.90 (d, 2H, J=4.0 Hz, H11), 7.51 (s, 2H, H6), 7.36 (s, 2H, H3), 7.22 (d, 2H, J=5.2 Hz, Harom), 7.02 (dd, 2H, J=3.6, 5.0 Hz, Harom), 6.98 (d, 2H, J=3.4 Hz, Harom), 6.88 (s, 2H, H9), 4.43-4.23 (m, 6H, H11a and OCH2CH2CH2O), 3.94 (s, 6H, OCH3×2), 3.59 (ddd, 2H, J=2.0, 11.5, 16.0 Hz, H1), 2.85 (ddd, 2H, J=1.5, 5.2, 16.0 Hz, H1), 2.49-2.40 (m, 2H, OCH2CH2CH2O).

Provenance & Evidence