trans-2-Methylcyclohexanol → ethyl (2Z)-2-[(1R,2S)-2-methylcyclohexyl]oxyimino-3-oxobutanoate

HRID 1194915Notes

Reaction equation

HRID 1194915 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][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1O>>[CH3:12][C@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[O:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 24004trans-2-MethylcyclohexanolHCID 178472876HCID 178472876, compound

Product 1

HCID 140352859ethyl (2Z)-2-[(1R,2S)-2-methylcyclohexyl]oxyimino-3-oxobutanoateYield 8.5%

Procedure

Ethyl (Z)-2-hydroxyimino-3-oxobutyrate (3.48 g) was reacted with trans-2-methylcyclohexanol as described in Example 4a, method 3 to give the title compound (0.476 g, 8.5%), as a colourless liquid, νmax (film) 2930, 1740 and 1690 cm-1, δH (CDCl3) 0.95 (3H, d, J 6.9 Hz), 1.34 (3H, t), 1.3-2.1 (9H, m), 2.40 (3H, s), 4.36 (2H, q), and 4.39 (1H, m).

Sources & evidence

ORD record
ord-42804d1308724f46b36cad389f0fb938
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

Loading…