Ethyl 5-(4-Aminophenyl)-2-Methyl-3-Furoate → Ethyl 5-(4-hydroxyphenyl)-2-methyl-3-furanecarboxylate

HRID 393278Notes

Reaction equation

HRID 393278 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([CH3:17])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=2)=[CH:8][CH:7]=1>O.OS(O)(=O)=O>[OH:2][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([CH3:17])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 2742184Ethyl 5-(4-Aminophenyl)-2-Methyl-3-FuroateHCID 23668193Sodium Nitrite

Product 1

HCID 22648859Ethyl 5-(4-hydroxyphenyl)-2-methyl-3-furanecarboxylateYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (111 mg, 1.61 mmol) in water (1 mL) was added over 5 min to an ice-cold suspension of ethyl 5-(4-aminophenyl)-2-methyl-3-furanecarboxylate (395 mg, 1.61 mmol) in aqueous 1 M H2SO4 solution (12 mL). The reaction mixture was stirred at 0° C. for 20 min then was heated to 90° C. for 1 h. The cooled mixture was extracted with EtOAc. The organic layer was washed with water (2×) and brine, dried (MgSO4), filtered and concentrated under reduced pressure to yield the title compound (78 mg, 20% yield) as a white solid.

Workup

  1. temperaturethen was heated to 90° C. for 1 h
  2. extractionThe cooled mixture was extracted with EtOAc
  3. washThe organic layer was washed with water (2×) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-371b50119d0c4c279cf533262f1fe6ab
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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