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

HRID 2245793노트

반응식

HRID 2245793 반응식
[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]

참가 물질

7

반응물 2

HCID 11725342HCID 11725342, 화합물HCID 23667635Sodium periodate

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b732062c0b84784bb7b3aef7b6e32b1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683185B2

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