3-Methylcyclohexanol → HCID 154041576, compound

Participants

Reaction Steps

Ethyl (Z)-2-hydroxyimino-3-oxobutyrate (3 g, 18.9 mmol) was converted into the title compound by reaction with 3-methylcyclohexanol (5.16 ml, 39.7 mmol. 60:40 cis: trans mixture) as described in Example 4a method 3, except that the reaction was complete in 2 h. After purification the title compound was obtained as a colourless oil (2.4 g; 50%); νmax (CHCl3) 1740, 1685, and 1590 cm-1 ; δH (CDCl3) 0.75-0.97 (1H, m), 0.96 (3H, d, J 6.5 Hz), 1.05 (1H, dd, J 11.7 Hz, partially obscured by d, δ 0.96), 1.32 (3H, t, J 7. 1 Hz), 1.19-1.40 (2H, m, partially obscured by t, δ 1.32), 1.40-1.73 (2H, m), 1.79-1.90 (1H, m), 2.03-2.19 (2H, m), 2.39 (3H, s), 4.23 (1H, tt, J 11.2 and 4.5 Hz), and 4.34 (2H, q, J 7.1 Hz); δ13C 14.1, 22.3, 23.6, 25.1, 31.2, 31.4, 34.0, 40.1, 61.7, 85.1, 149.9 161.5, and 193.

Provenance & Evidence