1-Bromo-1-methylcyclohexane → ethyl (2Z)-2-(1-methylcyclopentyl)oxyimino-3-oxobutanoate
Reaction equation
[OH:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15]C1>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:19][C:13]1([O:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:15][CH2:16][CH2:17][CH2:18]1Participants
4
Procedure
Ethyl (Z)-2-(hydroxyimino)-3-oxobutyrate (5.86 g, 36.8 mmol), 1-bromo-1-methylcyclohexane (6.01 g 36.8 mmol), and silver trifluoromethanesulphonate (9.45 g, 36.8 mmol) were reacted together by a similar method to that described in Example 9a to give the title compound (4.45 g, 50%); νmax (film) 2970, 1745, 1690, 1590, 1370, 1320, 1230, 1070, and 990 cm-1 ; δH (60 MHz, CDCl3), 1.31 (3H, t, J 7 Hz), 1.48 (3H, s), 1.1-2.2 (8H, m), 2.35 (3H, s), and 4.30 (2H, q, J 7 Hz).