HCID 21217007, compound → HCID 21217003, compound

HRID 1586529Notes

Reaction equation

HRID 1586529 reaction equation
[CH2:1]([C:7]1[C:8]([C:32](OCC)=[O:33])=[C:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:11]([C:13](OCC)=[O:14])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C:7]1[C:8]([CH2:32][OH:33])=[C:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:11]([CH2:13][OH:14])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 21217007HCID 21217007, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21217003HCID 21217003, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 250 mL 3 neck round-bottom flask equipped with a condenser was flushed with nitrogen and then loaded with diethyl 5-hexyl-2,3-di-(4-fluorophenyl)-1,4-benzenedicarboxylate (4 g, 8.1 mmol), anhydrous THF (40 mL) and then cooled in an ice/water bath. Lithium aluminum hydride (1.23 9, 32.4 mmol) followed by THF (40 mL) was added to the reaction mixture with stirring. The mixture was warmed to room temperature and then refluxed for 6 hours. This was then cooled to room temperature and the excess lithium aluminum hydride was destroyed by dropwise addition of water. NaOH (1.5 g in 10 mL of water) was then added and stirred for 15 min. The solvent was then removed by rotary evaporation and then 10% sulfuric acid (80 mL) was added to the white gelatinous product and stirred overnight. The white precipitate was filtered and washed with water and air-dried (3.12 g, 94.0% yield).

Workup

  1. customwas flushed with nitrogen
  2. temperaturecooled in an ice/water bath
  3. additionwas added to the reaction mixture
  4. temperaturerefluxed for 6 hours
  5. temperatureThis was then cooled to room temperature
  6. customthe excess lithium aluminum hydride was destroyed by dropwise addition of water
  7. additionNaOH (1.5 g in 10 mL of water) was then added
  8. stirringstirred for 15 min
  9. customThe solvent was then removed by rotary evaporation
  10. addition10% sulfuric acid (80 mL) was added to the white gelatinous product
  11. stirringstirred overnight
  12. filtrationThe white precipitate was filtered
  13. washwashed with water
  14. customair-dried (3.12 g, 94.0% yield)

Sources & evidence

ORD record
ord-77cc58a14b9145ff8126369c585022e7
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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