1-Bromobicyclo(2.2.2)octane → ethyl (2Z)-2-(1-bicyclo[2.2.2]octanyloxyimino)-3-oxobutanoate

HRID 1194900Notes

Reaction equation

HRID 1194900 reaction equation
Br[C:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[OH:10]/[N:11]=[C:12](/[C:18](=[O:20])[CH3:19])\[C:13]([O:15][CH2:16][CH3:17])=[O:14]>FC(F)(F)S([O-])(=O)=O.[Ag+]>[C:2]12([O:10]/[N:11]=[C:12](/[C:18](=[O:20])[CH3:19])\[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 1390601-Bromobicyclo(2.2.2)octaneHCID 178472876HCID 178472876, compound

Product 1

HCID 14864974ethyl (2Z)-2-(1-bicyclo[2.2.2]octanyloxyimino)-3-oxobutanoateYield 22.6%

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

1-Bromobicyclo[2.2.2]octane (4.6 g, 24.3 mmol), ethyl (Z)-2-hydroxyimino-3-oxobutyrate (3.78 g, 24.3 mmol) and silver trifluoromethanesulphonate (6.32 g, 24.6 mmol) were reacted under similar conditions to that described in Example 31a to give the title compound (1.47 g, 22%); νmax (CH2Cl2) 2950, 2925, 2860, 1735, 1685, 1370 and 1325 cm-1 ; δH (60 MHz, CDCl3) 1.30 (3H, t, J ca 7 Hz), 1.64 (S) and 1.75 (s) (together 13H), 2.36 (3H, s), and 4.30 (2H, q); [Ammonia CI mass spectrum Found MH+ (288)].

Sources & evidence

ORD record
ord-645b50a1ef9e428ba1a5d6d398bda21e
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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