Tetrahydrofuran → HCID 67264114, compound

HRID 1687625Notes

Reaction equation

HRID 1687625 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)C.C1COCC1.[OH-].[Na+]>>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[C:8]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67263879HCID 67263879, compound

Product 1

HCID 67264114HCID 67264114, compoundYield 80.1%

Procedure

(4-Nitro-2-pyrrol-1-yl-phenoxy)-acetic acid ethyl ester (15 g, 0.052 mol), THF (100 mL, 1 mol), and Sodium hydroxide (10 mL, 0.5 mol) were stirred at rt for 6 h. The reaction mixture was concentrated, diluted with H2O, and washed with EtOAc. The aqueous layer was neutralized and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to afford 10.92 g (80%) of a yellow oil which solidified upon standing.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d86f567dff234e4ca4359fc1e1a1bbb8
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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