Compound 6c

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Compound data: CIF

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

The title compound was synthesised following the general method for arylative spirocyclization outlined in the synthesis of 6a, using p-tolylmagnesium bromide solution (4.80 mL of a 0.50 M solution in THF generated using the general method outlined in the synthesis of 6a, 2.40 mmol) and Fe(acac)₃ (17.7 mg, 0.05 mmol). The crude product was isolated as a >95:5 mixture of diastereoisomers. Purification by flash chromatography, eluting with CH₂Cl₂:hexane (60:40), gave compound 6c as a colourless solid (0.25 g, 94%) as a single diastereoisomer.mp 77.3-78.5 ˚C; R_f 0.22 (CH₂Cl₂:hexane, 60:40); ¹H NMR (CDCl₃) δ^H 2.36 (s, 3H), 4.52 (d, J 10.5, 1H), 4.60 (d, J 10.5, 1H), 5.96-6.00 (m, 2H), 6.18 (dd, J 1.2 5.6, 1H), 6.89 (d, J 8.4, 1H), 6.97 (t, J 7.4, 1H), 7.17-7.30 (m, 6H); ¹³C NMR (CDCl₃) δ^C 21.2, 80.5, 87.3, 95.9, 110.7, 121.1, 124.4, 126.6, 128.2, 128.9, 129.3, 130.7, 132.2, 137.9, 138.0, 160.2; ν_max (thin film, cm^-1) 1598, 1475, 1177; m/z [C₁₈H₁₆O₂Na]⁺ expected 287.1048, found 287.1042.