Triethylamine → (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide

HRID 445820Notes

Reaction equation

HRID 445820 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.F[B-](F)(F)F.[N:20]1([O:29][C:30](N(C)C)=[N+](C)C)[C:24]2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C.O>[CH3:30][O:29][N:20]([CH3:24])[C:12](=[O:14])[CH2:11]/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 14713049(E)-4-(4-methoxyphenyl)but-3-enoic acid

Product 1

HCID 22347543(E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamideYield 30.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the mixture of carboxylic acid (557) (5.7 g, 29.5 mmol) in DMF (150 mL) was added O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (9.5 g, 29.5 mol). After stirring for 5 minutes, N,O-dimethylhydroxylamine. HCl (2.9 g, 29.5 mmol) was added, followed by Et3N (8.2 mL, 58.9 mmol). The reaction mixture was stirred at room temperature for 3 hours, diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes) to provide (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide (558) (2.1 g, 29.6%) as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3edd51bf58c041b387f8b6e4e13eb253
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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