1-Cyclohexene-1-carboxaldehyde → HCID 68915927, compound

The product was prepared by General procedure L using 0.28 mL (0.55 mmol, 2.0 M in hexanes) Et2Zn, 4.8 mg (0.02 mmol) (−)-MIB, and 55 mg (0.50 mmol) cyclohexenecarboxaldehyde. The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes) to afford the title compound in 90% yield (104 mg, 0.39 mmol) as a colorless oil, [α]D20=−3.4 (c=0.005, CHCl3, 99% ee); 1H NMR (CDCl3, 500 MHz): δ 0.8 (t, 3H, J=7.5 Hz), 1.3 (br s, 2H), 1.5-1.6 (m, 4H), 1.8 (s, 1H), 2.0 (s, 4H) 3.84 (q, 1H, J=10.0 Hz), and 5.63 (s, 1 H) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 10.1, 22.6, 23.3, 24.9, 27.6, 29.6, 78.1, 123.2, and 139.6 ppm; IR (neat) 3500, 2962, 2922, 2874, 2360, 1732, 1456, and 1260 cm−1. HRMS-CI m/z 123.1174 [(M−OH)+; calcd for C9H15: 123.1173].

1. customThe product was prepared by General procedure L
2. customThe crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes)

ORD record

ord-61acbe9aa754428c9f7b0346de189f3d

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236976B2