Isobutyl (E)-4-oxo-2-butenoate → Isobutyl 4-oxobutanoate

HRID 654111Notes

Reaction equation

HRID 654111 reaction equation
[O:1]=[CH:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6]>C(O)C.[Pd]>[O:1]=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6]

Participants

4

Reactant 1

HCID 10057752Isobutyl (E)-4-oxo-2-butenoate

Product 1

HCID 10464575Isobutyl 4-oxobutanoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of isobutyl (E)-4-oxo-2-butenoate (97 g, 0.62 mol) in 96% ethanol (800 ml), 5% palladium on charcoal (9.7 g) was added and hydrogen was bubbled at 5°-10° C. and at atmospheric pressure for 20 hours. Removal of the catalyst and evaporation of the solvent gave 97.6 g (99%) of the title compound; Rf=0.41 (silica gel plates, eluent: cyclohexane-ethvl- acetate 6:4). NMR (CDCl3): deltaH =12.5 (d, J=1 Hz, 1H, CHO); 3.85 (d, J=6 Hz, 2H, COOCH2); 2.80-2.40 (c.a., 4H, CH2CH2CO); 2.10-1.70 (c.a., 1H, CH2CHMe2); 0.90 (d, J=6 Hz, 6H, CH3). MS (E.I., 70 eV, 1.5 mA) m/z=103 (M--C3H3O)+, 85 (M--C3H5O2)+, 57 (M--C4H5O3)+.

Workup

  1. customhydrogen was bubbled at 5°-10° C. and at atmospheric pressure for 20 hours
  2. customRemoval of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-651803adffac4f709a48d47bb036d485
Source dataset
uspto-grants-1992_07
Patent number
US05130319

Reaction notes

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