trans-2-Hexenal → Diacetyl(methoxyimino)methane

HRID 2390955Notes

Reaction equation

HRID 2390955 reaction equation
[C:1]([O:4][N:5]=[C:6]([C:10](=[O:12])[CH3:11])[C:7](=[O:9])[CH3:8])(=O)C.C(=O)/C=C/CCC>C1(C)C=CC=CC=1.C(NC(C)C)(C)C>[CH3:1][O:4][N:5]=[C:6]([C:10](=[O:12])[CH3:11])[C:7](=[O:9])[CH3:8]

Participants

5

Reactant 2

HCID 5281168trans-2-HexenalHCID 130858783-(Acetoxyimino)pentane-2,4-dione

Product 1

HCID 536122Diacetyl(methoxyimino)methane

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 3-(acetoxyimino)pentane-2,4-dione 12 (0.2 mmol, 1.0 eq) and (E)-hex-2-enal (0.5 mmol, 2.5 eq) in toluene (0.8 mL) was added catalyst VII (0.04 mmol, 0.2 eq) in toluene (0.2 mL) at room temperature. The resulting mixture was stirred vigorously. After 12 hours the reaction still didn't proceed.

Workup

  1. customAfter 12 hours the reaction

Sources & evidence

ORD record
ord-1b8fa70e128c4b2c94e38f1b566e9919
Source dataset
uspto-grants-2012_09
Patent number
US08273901B2

Reaction notes

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