Sodium Hydroxide → HCID 57706373, compound

HRID 1662518Notes

Reaction equation

HRID 1662518 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14](OC)=[O:15])=[CH:10][C:9]=2[C:18]2[C:22]([CH3:24])([CH3:23])[CH2:21][CH2:20][CH:19]=2)[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=2[C:18]2[C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][CH:19]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706006Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706373HCID 57706373, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 78.9A (0.082 g, 0.23 mmol) in THF (5.00 mL) at 0° C. was added LAH (0.46 mL, 0.46 mmol, 1.0M). The reaction was then stirred for 1.5 hours. 1N NaOH(aq) was then added to the quench the reaction. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-20% EtOAc in hexanes) to yield 78.9B as a colorless oil (0.048 g, 63% yield).

Workup

  1. customquench
  2. customthe reaction
  3. extractionThe reaction was extracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3461c1161d9f4be7812f8081b85d9791
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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