2-(4-Amino-3-methylphenoxy)ethan-1-ol → Ethyl 2-{[4-(2-hydroxyethoxy)-2-methylphenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate

HRID 402641Notes

Reaction equation

HRID 402641 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([CH3:12])[CH:6]=1.C(O[C:16]1[O:17][CH2:18][C:19](=[O:26])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C(O)C>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:16]2[O:17][CH2:18][C:19](=[O:26])[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([CH3:12])[CH:6]=1

Participants

4

Reactant 2

HCID 4592592-(4-Amino-3-methylphenoxy)ethan-1-olHCID 13791062Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Product 1

HCID 86708330Ethyl 2-{[4-(2-hydroxyethoxy)-2-methylphenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(2-hydroxyethoxy)-2-methylaniline (0.69 g, 4.1 mmol) and ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.83 g, 4.2 mmol) in ethanol (8.3 mL) was stirred at ambient temperature for 16 h. The solvent was removed under reduced pressure, and ethanol was added to precipitate the product. The precipitate was collected by filtration then dried to afford ethyl 2-{[4-(2-hydroxyethoxy)-2-methylphenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.55 g, y. 42%).

Workup

  1. customThe solvent was removed under reduced pressure, and ethanol
  2. additionwas added
  3. customto precipitate the product
  4. filtrationThe precipitate was collected by filtration
  5. customthen dried

Sources & evidence

ORD record
ord-c3e10ebeaaae4ecd8bcafe53c4dc3358
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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