Dimethylformamide → 538-65-8

HRID 589527Notes

Reaction equation

HRID 589527 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:12][C:13](=[O:16])[CH:14]=[CH2:15])[CH2:9][CH2:10][CH3:11].C(N(C(C)C)C(C)C)C.CN(C=O)C>C(OCC)(=O)C.[Pd]>[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8846Butyl AcrylateHCID 11575IodobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 5273465538-65-8Yield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 8857Ethyl AcetateSolvent

Procedure

The Pd/C monolith (42 mg of a 1% Pd/C monolith, 2 mol % Pd) prepared according to the method described in Example 2 was added to a 1 dram glass vial in air followed by iodobenzene (28 μL, 0.25 mmol), n-butylacrylate (54 μL, 0.375 mmol), ethyldiisopropylamine (1.5 equiv, 0.375 mmol, 65 μL) and 1 mL DMF. The vial was sealed under air with a rubber septum cap and placed in an oil bath preheated to 80° C. for 24 hours. After the allotted time, the reaction mixture was dissolved in ethyl acetate. Gas chromatographic analysis indicated a 71% yield of (E)-n-butyl cinnamate.

Workup

  1. customThe vial was sealed under air with a rubber septum
  2. customcap
  3. customplaced in an oil bath

Sources & evidence

ORD record
ord-7e11c343222f4046958267a5ce80a5e8
Source dataset
uspto-grants-2016_01
Patent number
US09233366B2

Reaction notes

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