Tetrahydrofuran → 3-[(4-Chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)-1-propanol

HRID 748761Notes

Reaction equation

HRID 748761 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH2:23][C:24](OCC)=[O:25])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCOCC.C(OCC)(=O)C.CCCCCC>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH:22]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH2:23][CH2:24][OH:25])(=[O:21])=[O:20])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59750785Ethyl 3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propionate

Product 1

HCID 230287923-[(4-Chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)-1-propanolYield 34%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Process 1: At 0° C., lithium aluminum hydride (a 1.0M tetrahydrofuran solution, 6.74 ml, 6.74 mmol) was added dropwise to a tetrahydrofuran solution (10 ml) of the ethyl 3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propionate (1.31 g, 3.37 mmol) obtained in Example 25. The mixture was then was stirred at room temperature for 3 hours. After cooling the reaction mixture to 0° C., and addition of a saturated aqueous ammonium chloride solution, the mixture was stirred at room temperature for 15 hours. The solid thus precipitated was filtered off. The solution thus obtained was diluted with ether, washed with brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (397 mg, 1.14 mmol, 34%) was obtained as a colorless solid.

Workup

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. customThe solid thus precipitated
  4. filtrationwas filtered off
  5. customThe solution thus obtained
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-51223136fe184a33a7b2242dac9e9584
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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