Toluene → HCID 53997352, compound

HRID 1081968Notes

Reaction equation

HRID 1081968 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[NH:8].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11].C(N(C(C)C)CC)(C)C.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].[C:30]1(C)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[CH3:14][O:13][C:9]([CH:10]1[CH:7]([N:8]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:3]2[O:4][CH:5]=[CH:6][C:2]=2[CH2:1][CH2:11]1)=[O:12]

Participants

7

Reactant 5

HCID 1140TolueneHCID 7294Methyl AcrylateHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 86750093HCID 86750093, compound

Product 1

HCID 53997352HCID 53997352, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-methylfuran-2-carboxaldehyde imine (1.5 g, 8.15 mmol), methyl acrylate (3.5 g, 40.7 mmol) and diisopropyl ethyl amine (2.1 g, 16.3 mmol) were mixed in toluene (6 ml) and stirred at 80° C. Ethyl chloroformate (1.77 g, 16.3 mmol) was added to the mixture. After completing the addition, the reaction mixture was heated for one hour under reflux and allowed to cool to room temperature. Water was added and the mixture was extracted with toluene. The organic layer was washed with an aqueous solution of sodium chloride and dried over sodium sulfate. The solvent was distilled off to obtain crude products of N-ethoxycarbonyl-N-phenyl-7-amino-4,5,6,7-tetrahydrobenzo[b]furan-6-carboxylic acid methyl ester. Silica gel column chromatography using a developing solvent of hexane/ethyl acetate=5/1, gave a fraction containing the desired product, which was concentrated by distilling off the solvent, to obtain 1.2 g (yield: 43.0% from imine) of N-ethoxycarbonyl-N-phenyl-7-amino-4,5,6,7tetrahydrobenzo[b]furan-6-carboxylic acid methyl ester. 1H-NMR spectra (chemical shift, ppm: in CDCl3): 1.00-1.40 (3H, m), 1.65-2.10 (2H, m), 2.15-3.05 (joined 2H, m), 3.74 (3H, s), 3.95-4.30 (3H, m), 5.75-6.20 (joined 1H, m), 6.50-6.95 (2H, m), 7.00-7.50 (5H, m).

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was heated for one hour
  3. temperatureunder reflux
  4. temperatureto cool to room temperature
  5. extractionthe mixture was extracted with toluene
  6. washThe organic layer was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8ab0632e577f4b0d845b21a4aa823919
Source dataset
uspto-grants-1996_12
Patent number
US05587486

Reaction notes

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