Sodium Hydroxide → 5-Fluoro-2-(4-fluorophenyl)-2,3-dihydro-2-hydroxy-1H-inden-1-one

HRID 1440805Notes

Reaction equation

HRID 1440805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:5]2.C([O:21]P(OCC)OCC)C.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)([OH:21])[CH2:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31215Triethyl phosphiteHCID 199754355-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 199754325-Fluoro-2-(4-fluorophenyl)-2,3-dihydro-2-hydroxy-1H-inden-1-oneYield 38.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 7.0 g (0.029 moles) of the product obtained from Step A and 69 mL of toluene was added with stirring to a mixture of 5.7 g (0.034 moles) of triethylphosphite, 0.33 g (0.0014 moles) of benzyltriethylammonium chloride, 344 mL of toluene and 167 mL of 50% aqueous sodium hydroxide solution. A steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour. The resulting mixture was partitioned between hexane/ether and water and the aqueous layer was extracted three times with ether. The combined organic layers were washed twice with water, three times with saturated aqueous sodium bisulfite solution, dried over magnesium sulfate and concentrated. The resulting crude product was triturated several times with hexanes to afford 2.93 g of a pale yellow solid.

Workup

  1. additionA steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour
  2. customThe resulting mixture was partitioned between hexane/ether and water
  3. extractionthe aqueous layer was extracted three times with ether
  4. washThe combined organic layers were washed twice with water, three times with saturated aqueous sodium bisulfite solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was triturated several times with hexanes

Sources & evidence

ORD record
ord-2bf0ec106deb4791b84c0b986f1b8d74
Source dataset
uspto-grants-1996_03
Patent number
US05500438

Reaction notes

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