3-Methylcyclohexanol → HCID 154041576, compound

HRID 1194934Notes

Reaction equation

[OH:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15](O)[CH2:14]1>>[CH3:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([O:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:14]1

Participants

Reactant 2

HCID 115663-Methylcyclohexanol

HCID 178472876HCID 178472876, compound

Product 1

HCID 154041576HCID 154041576, compound

Procedure

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.

Sources & evidence

ORD record: ord-944d2407dc0e479b8ac8a569d23945c4
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816452

Reaction notes

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