Ethyl Acetate → 1-Benzyl-3-hydroxy-3-(4-hydroxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-one

Participants

Reaction Steps

Dissolve 1-benzyl-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-3-hydroxy-1,3-dihydro-indol-2-one (152 mg, 0.3 mmol) in THF (5 mL) and treat with 1.0M in THF tetrabutylammonium fluoride (0.36 mL, 0.36 mmol) for 6 h. Pour into ethyl acetate (25 mL) and wash with water (3×25 mL) and brine (25 mL). Dry (MgSO4), filter and concentrate in vacuo to give a summy residue. Purify by flash chromatography (gradient of 5% EtOAc/hexanes to 50% EtOAc/hexanes) to give 116 mg (98%) of the title compound as a white solid. MS (ES): m/z=376 (M+1−H2O); 1H NMR(DMSO-d6); δ8.26 (s, 1H), 7.54 (dd, J=1.7, 1.4 Hz, J=7.7, 7.4 Hz, 1H), 7.38-7.15 (m, 5H), 7.05 (t, J=7.4 Hz, 1H), 6.85 (m, 3H), 6.65 (s, 1H), 4.96 (q, 2H), 2.12 (s, 6H).

Provenance & Evidence