Potassium Carbonate → 4-(4-Aminophenoxymethyl)-2-methoxycarbonyl-furan

HRID 1474821Notes

Reaction equation

HRID 1474821 reaction equation
[N+](C1C=C(O)C=CC=1)([O-])=O.[N+:11]([C:14]1[CH:30]=[CH:29][C:17]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[O:23][CH:24]=2)=[CH:16][CH:15]=1)([O-])=O.ClCC1OC(C(OC)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[NH2:11][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[O:23][CH:24]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 87336271HCID 87336271, compound

Product 1

HCID 220608754-(4-Aminophenoxymethyl)-2-methoxycarbonyl-furanYield 101.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Preparation of 4-(4-nitrophenoxymethyl)-2-methoxycarbonyl-furan 3-Nitrophenol (1.0 g, 7.19 mmole), methyl 5-(chloromethyl)-2-furoate (1.38 g, 7.90 mmole) and anhydrous K2CO3 (1.19 g, 8.60 mmole) in acetone (30 mL) were refluxed for 8 h. The reaction mixture was cooled and diluted with water. The resultant white solid was filtered, washed with water and air dried overnight to give 1.81 g (90%) of the desired product. 1H NMR (CDCl3): δ 7.86 (dd, 1H, J=2.3 and 8.2 Hz), 7.80 (t, 1H, J=2.3 Hz), 7.45 (t, 1H, J=8.2 Hz), 7.27 (dd, 1H, J=2.3 and 8.2 Hz), 7.17 (d, 1H, J=3.5 Hz), 6.58 (d, 1H, J=3.5 Hz), 5.13 (s, 2H), 3.90 (s, 3H).

Workup

  1. temperaturewere refluxed for 8 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resultant white solid was filtered
  4. washwashed with water and air
  5. customdried overnight

Sources & evidence

ORD record
ord-c9d8445ed90e420b83d85e49a6147227
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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