Tetrahydrofuran → HCID 23062483, compound

HRID 2109386Notes

Reaction equation

HRID 2109386 reaction equation
CCN=C=NCCCN(C)C.C1COCC1.[OH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28].[F:30][C:31]1[C:36](O)=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41]>O>[OH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O:24][C:36]2[C:35]([F:38])=[C:34]([F:39])[C:33]([F:40])=[C:32]([F:41])[C:31]=2[F:30])=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 120334-Hydroxy-3-nitrobenzoic acidHCID 13041PentafluorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 23062483HCID 23062483, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

WSC (7.9 g) was added to a THF (100 ml) solution of 4-hydroxy-3-nitrobenzoic acid (7.3 g). and pentafluorophenol (7.4 g) at 0° C., and stirred overnight at 25° C. Water (50 ml) was added to the reaction solution, the solvent was evaporated under reduced pressure, and the organic layer was extracted with ethyl acetate. After drying the organic layer over MgSO4, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4), thereby giving 7.9 g of the desired compound.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionthe organic layer was extracted with ethyl acetate
  3. dry with materialAfter drying the organic layer over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-754d7ddaeecd49b8a0922df41d4383d2
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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