Tetrahydrofuran → HCID 10174371, compound

Participants

Reaction Steps

Dissolve 3,3-bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (150 mg, 0.25 mmol) in anhydrous DMF (1.5 mL) under nitrogen. Add slowly a 1M solution of potassium t-butoxide in THF (0.260 mL, 0.260 mmol). Stir 5 min and add 4-methoxybenzyl chloride (0.037 mL, 0.275 mmol). After 1 h add a 1M solution of tetrabutylammonium fluoride in THF (0.625 mL, 0.625 mmol) and stir 2 h. Dilute with water (10 mL) and extract with ethyl acetate (3×15 mL). Wash combined organic portions with water, brine, dry (Na2SO4), filter and concentrate in vacuo to obtain 161 mg of a residue. Recrystallize from CH2Cl2 and hexane to obtain 63 mg (51%) of the title compound as a white solid. MS (ES): m/z=494 (M+1), 492 (M−1); 1H NMR(DMSO-d6): δ8.24 (s, 2H), 7.30-7.20 (m, 4H), 7.04 (m, 2H), 6.89 (d, J=8.7 Hz, 2H), 6.68 (s, 4H), 5.77 (s, 2H), 3.72 (s, 3H), 2.07 (s, 12H).

Provenance & Evidence