HCID 12939510, compound → HCID 14864972, compound

HRID 1194899Notes

Reaction equation

HRID 1194899 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([CH3:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCOCC1.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:20][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])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 12939510HCID 12939510, compoundHCID 178472876HCID 178472876, compound

Product 1

HCID 14864972HCID 14864972, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl (Z)-2-hydroxyimino-3-oxobutyrate (795 mg, 5 mmol) and 1-bromo-1-methylcycloheptane (1.lg, 5.76 mmol) in dry 1,4-dioxan (5 ml) under an atmosphere of argon in the dark were treated portionwise with silver trifluoromethanesulphonate (1.48 g, 5.76 mmol), with stirring, over 5 h. The mixture was stirred for a further 18 h in the dark and then worked up using a similar procedure to that described in Example 7a to give the title compound as an oil (878 mg; 65%); νmax (CH2Cl2) 3430, 3350, 1740, 1685, 1595, 1370, 1320, 1230, 1070, and 1,000cm-1 ; δH (250 MHz, CDCl3) 1.33 (3H, t, J 7.1Hz), 1.33 (3H, s), 1.4-1.8 (1OH, m), 1.99 (2H, dd, J ca 13.5 and 7.5 Hz), 2.40 (3H, s), and 4.35 (2H, q, J 7.1 Hz); [Found: M30 -OEt 224.1273. C12H18NO3 requires M-OEt 224.1287. Ammonia CI mass spectrum MH+ (270)].

Workup

  1. stirringThe mixture was stirred for a further 18 h in the dark and

Sources & evidence

ORD record
ord-7c597bcc060743dc9ea6ffa4a0c3b5f1
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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