Water → Methyl 4-acetamido-3-methoxycinnamate

HRID 613597Notes

Reaction equation

HRID 613597 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2].C1(P(=[CH:34][C:35]([O:37][CH3:38])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:34][C:35]([O:37][CH3:38])=[O:36])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 183218014-Acetamido-3-methoxybenzaldehyde

Product 1

HCID 54551695Methyl 4-acetamido-3-methoxycinnamateYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-acetamido-3-methoxybenzaldehyde (388 mg) in tetrahydrofuran (10 ml) was added methyl (triphenylphosphoranylidene)acetate (739 mg), and the mixture was stirred for 2 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=30:1, V/V) to give methyl 4-acetamido-3-methoxycinnamate (113 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1, V/V)

Sources & evidence

ORD record
ord-1974e177315145c08363aa2acd54c231
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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