HCID 11725342、化合物 → 6-(4'-Chloro-biphenyl-4-ylsulfinyl)-hexanoic acid methyl ester

HRID 2245793ノート

反応式

HRID 2245793 の反応式
[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]

参加物

7

反応物 2

HCID 11725342HCID 11725342、化合物HCID 23667635Sodium periodate

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b732062c0b84784bb7b3aef7b6e32b1
出典データセット
uspto-grants-2010_03
特許番号
US07683185B2

反応ノート

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