Compound 3d

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InChIKey GORJQLGRSWQMDM-UHFFFAOYSA-N

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

Following the general procedure for compound 3b, 8.27 g (73.1 mmol) of isovaleraldehyde cyanohydrin was combined with 85.0 g of isobutylene (20.7 equiv, 1.51 mol) and 2.0 mL of methanesulfonic acid (0.40 equiv, 30.3 mmol) in a Parr shaker bottle to afford, after vacuum distillation, 6.92 g of 3d (56% yield, >96% purity by ¹H-NMR) as a clear, light yellow liquid. Analytically pure material was obtained after a vacuum to distillation over K₂CO₃ to afford 6.48 g of 3d (52%) as a clear, colorless liquid. bp: 63 - 65 °C (8.6 mm Hg); ¹H NMR: (500 MHz, CDCl₃) 4.19 (dd, J=8.1, 6.3 Hz, 1 H, HC(2)), 1.88 – 1.76 (m, 1 H, HC(4)), 1.72 – 1.56 (m, 2 H, H₂C(3)), 1.27 (s, 3 H, H₃C(7)), 0.94 (d, J=6.7 Hz, 3 H, H₃C(5)), 0.92 (d, J=6.6 Hz, 3 H, H₃C(5)); ¹³C NMR: (125 MHz, CDCl₃) 121.20 (C(1)), 76.18 (C(6)), 59.33 (C(2)), 43.91 (C(3)), 27.58 (C(7)), 24.03 (C(4)), 22.51 (C(5)), 22.01 (C(5)); IR: (KBr Pellet) 2962 (s), 2874 (s), 1469 (m), 1393 (m), 1370 (s), 1260 (m), 1238 (m), 1191 (s), 1128 (m), 1078 (s), 1023 (m), 1003 (w), 961 (w), 906 (w), 884 (w), 834 (w), 738 (w); MS: (EI, 70 meV) 154.1 (38.7), 96.1 (35.6), 69.1 (12.9), 59.1 (100.0), 57.1 (91.4), 54.1 (25.2); Analysis: C₁₀H₁₉NO (169.26) Calcd: C, 70.96; H, 11.31; N, 8.28% Found: C, 70.74; H, 11.42; N, 8.12%.