Tetrahydrofuran → HCID 53629726, compound

HRID 2381249Notes

Reaction equation

HRID 2381249 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([C:6]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([OH:17])[C:11]([OH:18])=[CH:10][C:7]=1[C:8]#[N:9])=[O:5].O1CCCC1.[C:28](Cl)(=[O:32])[O:29][CH2:30][CH3:31].C(N(CC)CC)C.[C:41]([O:44][CH2:45][CH3:46])(=[O:43])C>>[CH2:30]([O:29][C:28]([O:17][C:12]1[C:11]([O:18][C:41]([O:44][CH2:45][CH3:46])=[O:43])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:4](=[O:5])[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=2[F:1])[C:13]=1[N+:14]([O-:16])=[O:15])=[O:32])[CH3:31]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 58345633HCID 58345633, compound2×

Product 1

HCID 53629726HCID 53629726, compound

Procedure

To a mixture of 2-(2-fluorobenzoyl)-4,5-dihydroxy-3-nitrobenzonitrile (compound 1-29) (70 mg) and tetrahydrofuran (2.0 mL) were added ethyl chlorocarbonate (70 μl) and triethylamine (110 μl) under ice-bath cooling. After stirring for 30 minutes, the mixture was stirred at room temperature for 2 days. The mixture was diluted with ethyl acetate, and washed with 1 mol/L hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-30% ethyl acetate/hexane, gradient elution) to give the title compound (103 mg). The structural formula was illustrated in table 10.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 days
  3. washwashed with 1 mol/L hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: 0%-30% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-0424a95e9321478f9367e971821461db
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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