HCID 11725342, compound → 6-(4'-Chloro-biphenyl-4-ylsulfinyl)-hexanoic acid methyl ester

HRID 2245793Notes

Reaction equation

HRID 2245793 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:25].[Na+]>CO.O1CCCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[O:25]

Participants

7

Reactant 2

HCID 11725342HCID 11725342, compoundHCID 23667635Sodium periodate

Product 1

HCID 100673776-(4'-Chloro-biphenyl-4-ylsulfinyl)-hexanoic acid methyl esterYield 81%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(4′-chloro-biphenyl-4-ylsulfanyl)-hexanoic acid methyl ester (900 mg, 2.6 mmol) in methanol (30 mL) and tetrahydrofuran (20 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (608 mg, 2.8 mmol) in distilled water (8 mL). The mixture was heated at 60° C. for 2 hours. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL), distilled water (50 mL), then with brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (1:1 to 8:2 ethyl acetate:40-60° C. petroleum ether). The solid obtained was recrystallised from diethyl ether/40-60° C. petroleum ether to give the title compound (763 mg, 81%) as a solid, mp 64-65° C.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto give an oil that
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL)
  4. distillationdistilled water (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil that
  9. customwas purified by flash chromatography (1:1 to 8:2 ethyl acetate:40-60° C. petroleum ether)
  10. customThe solid obtained
  11. customwas recrystallised from diethyl ether/40-60° C. petroleum ether

Sources & evidence

ORD record
ord-4b732062c0b84784bb7b3aef7b6e32b1
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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