3-Methylbutanal → HCID 86632042, compound

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Reaction Steps

The product was prepared by General procedure S using 196 mg (1.1 mmol) Cy2BH, 137 μL (1.1 mmol) 3,3-dimethyl-1-butyne, 1.1 mL (2.1 mmol, 2.0 M in hexanes) Et2Zn, 9.6 mg (0.04 mmol) (−)-MIB, and 107 μL (1.0 mmol) isovaleraldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 86% yield (146 mg, 0.86 mmol). [α]D20=+16.7 (c=3.0, CHCl3, 85% ee); 1H NMR (CDCl3, 500 MHz): δ 0.88 (t, 6H, J=7.0 Hz), 0.97 (s, 9H), 1.26 (m, 1H), 1.43 (m, 1H), 1.50 (br s, 1H), 1.65 (m, 1H), 4.07 (dt, 1H, J=7.0, 6.8 Hz), 5.31 (dd, 1H, J=15.6, 7.2 Hz), and 5.61 (d, 1H, J=15.7 Hz) ppm; 13C{1H} NMR (CDCl3, 1.25 MHz): δ 22.5, 22.9, 24.6, 29.5, 32.5, 46.6, 71.5, 128.1, and 142.6 ppm; IR (neat): 3334, 3013, 2956, 2869, 2354, 2320, 1662, 1466, 1386, 1363, 1308, 1268, 1220, and 1202 cm−1; HRMS-CI m/z 170.1666 [M+; calcd for C11H22O: 170.1671].

Provenance & Evidence