Sodium Hydroxide → HCID 10454998, compound

HRID 2082575Notes

Reaction equation

HRID 2082575 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][S:14][C:15]2[CH:27]=[C:26]([F:28])[C:18]([O:19][CH2:20][C:21](OCC)=[O:22])=[C:17]([F:29])[CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][S:14][C:15]2[CH:16]=[C:17]([F:29])[C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:26]([F:28])[CH:27]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 10344448HCID 10344448, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10454998HCID 10454998, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 4-[2-(4-chlorophenylsulfonylamino)ethylthio]-2,6-difluorophenoxyacetate (0.46 g) and tetrahydrofuran (30 ml) was added under ice cooling lithium aluminum hydride (38 mg), and the mixture was stirred at room temperature for an hour. To the reaction mixture was added successively 10% aqueous sodium hydroxide solution (0.2 ml), ethyl acetate (30 ml) and anhydrous sodium sulfate (1 g), and the insolubles were removed by filtration. After evaporation of the filtrate under reduced pressure, the residue was chromatographed on silica gel column (ethyl acetate:hexane=1:1), and the desired fractions were collected and recrystallized from ethyl ether/isopropyl ether mixture to give 2-{4-[2-(4-chlorophenylsulfonylamino)ethylthio]-2,6-difluorophenoxy}ethanol (Compound No. 129).

Workup

  1. additionwas added under ice
  2. customthe insolubles were removed by filtration
  3. customAfter evaporation of the filtrate under reduced pressure
  4. customthe residue was chromatographed on silica gel column (ethyl acetate:hexane=1:1)
  5. customthe desired fractions were collected
  6. customrecrystallized from ethyl ether/isopropyl ether mixture

Sources & evidence

ORD record
ord-582ef42bbc8a4ceebd240d86c20776c9
Source dataset
uspto-grants-1993_02
Patent number
US05189211

Reaction notes

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