Compound 13

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InChIKey WCGIPLYDSNEKBM-UHFFFAOYSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A 20-mL Schlenk flask, containing a magnetic stirring bar, was flame-dried under vacuum and filled with nitrogen after cooling to room temperature. To this vessel were added 6acdf (25.5 mg, 0.045 mmol, 1.0 equiv), 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (32.7 μL, 0.135 mmol, 3.0 equiv) and THF (450 μL) under a stream of nitrogen. The contents were cooled to 0 °C, and to this flask was added slowly a solution of tetrabutylammonium fluoride in THF (200 μL, 1.0 M, 0.2 mmol). The resultant mixture was warmed to room temperature, and after stirring for 1 h, water (1 mL) was added to the mixture. After extraction with CH₂Cl₂, the organic layer was dried over Na₂SO₄ and the volatiles were removed under reduced pressure. The residue was purified by preparative thin-layer chromatography (hexane/CH₂Cl₂ = 3:2) to afford 13 (22.5 mg, 85% yield) as a white solid. ¹H NMR (600 MHz, CDCl₃): δ 7.72–7.70 (m, 1H), 7.52–7.48 (m, 2H), 7.42–7.38 (m, 2H), 7.33 (d, J = 7.8 Hz, 2H), 7.26 (dd, J = 6.6, 2.4 Hz, 2H, overlapping with the peak of CHCl₃), 7.10 (dd, J = 6.6, 1.8 Hz, 2H), 6.90–6.84 (m, 3H), 6.82–6.78 (m, 2H), 6.70 (dd, J = 6.6, 2.4 Hz, 2H), 6.40 (dd, J = 6.9, 2.4 Hz, 2H), 3.60 (s, 3H), 1.30 (s, 9H); ¹³C NMR (150 MHz, CDCl₃): δ 157.1, 149.2, 143.8, 140.2, 139.4, 139.2, 138.5, 136.6, 136.3, 132.7, 132.3, 132.2, 131.6, 131.5, 131.2, 130.8, 128.5 (q, ²J_CF = 33.2 Hz), 127.3, 126.8, 126.3, 126.0, 125.9, 125.6, 124.5 (q, ³J_CF = 2.9 Hz), 124.4, 124.3 (q, ¹J_CF = 273 Hz), 112.1, 55.0, 34.4, 31.3; HRMS (APCI) m/z calcd for C₄₀H₃₄F₃O [MH]⁺: 587.25563, found 587.25334.