HCID 21217002, compound → HCID 21217012, compound

HRID 1586526Notes

Reaction equation

HRID 1586526 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12](OCC)=[O:13])=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:7]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:4][OH:3])=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:8]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21217002HCID 21217002, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21217012HCID 21217012, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL 3 neck round-bottom flask equipped with a condenser and an addition funnel was flushed with nitrogen and then loaded with diethyl-2,3-di(4-fluorophenyl)-1,4-benzenedicarboxylate (1.22 g, 2.98 mmol) in anhydrous THF (25 mL). Lithium aluminum hydride (1.0 M in THF, 11.4 mL, 11.4 mmol) was then added dropwise via the addition funnel to the reaction mixture and the mixture was then refluxed overnight. The mixture was cooled to room temperature and the excess lithium aluminum hydride was destroyed by dropwise addition of water. 15% NaOH (1 mL) was then added followed by more water (3 mL). The mixture was filtered and the solvent was removed by rotary evaporation. The product was then dissolved in chloroform and filtered. Removal of the chloroform gave a white solid (0.45 g, 46% yield).

Workup

  1. customwas flushed with nitrogen
  2. temperaturethe mixture was then refluxed overnight
  3. customthe excess lithium aluminum hydride was destroyed by dropwise addition of water
  4. addition15% NaOH (1 mL) was then added
  5. filtrationThe mixture was filtered
  6. customthe solvent was removed by rotary evaporation
  7. dissolutionThe product was then dissolved in chloroform
  8. filtrationfiltered
  9. customRemoval of the chloroform

Sources & evidence

ORD record
ord-b62f1149258240739f78f5babb2ba51b
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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