Potassium Carbonate → HCID 58260011, compound

Participants

Reaction Steps

The mixture of 6-hydroxy-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.42 g, 1.23 mmol), potassium carbonate (0.22 g, 1.60 mmol) and methyl bromoacetate (0.15 mL, 1.60 mmol) in 2-butanone (10 mL) was refluxed for 15 h. The reaction mixture was concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford methyl({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetate (0.51 g, 87%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.33-7.26 (m, 1H), 7.15-7.00 (m, 3H), 6.64-6.59 (m, 1H), 6.51 (d, J=2.4 Hz, 1H), 6.36 (dd, J=8.4, 2.4 Hz, 1H), 4.95 (d, J=9.0 Hz, 1H), 4.72 (d, J=9.0 Hz, 1H), 4.59 (s, 2H), 4.32-4.24 (m, 1H), 3.99-3.66 (m, 7H), 2.07-1.84 (m, 3H), 1.78-1.64 (m, 1H); MS (ES+) m/z 409.9 (M+1), 447.9 (M+39).

Provenance & Evidence