Tetramethylene sulfoxide → 4-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-benzoyloxy-1,1,3,3,3-pentafluoro-propane-1-sulfonate

HRID 1907085

反応式

HRID 1907085 の反応式
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH2:17]1[S:21](=O)[CH2:20][CH2:19][CH2:18]1.C(OC(C)C)(C)C.[C:30]([O:38][CH:39]([C:47]([F:50])([F:49])[F:48])[C:40]([F:46])([F:45])[S:41]([O-:44])(=[O:43])=[O:42])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>[C:30]([O:38][CH:39]([C:47]([F:49])([F:50])[F:48])[C:40]([F:45])([F:46])[S:41]([O-:44])(=[O:43])=[O:42])(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1.[F:1][C:2]([F:15])([F:16])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S+:21]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 1128Tetramethylene sulfoxideHCID 7914Diisopropyl EtherHCID 13443056HCID 13443056、化合物HCID 58112889Sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate

生成物 1

HCID 866642974-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-benzoyloxy-1,1,3,3,3-pentafluoro-propane-1-sulfonate収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid溶媒

実験手順

In 6 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 2.4 g (0.0107 mol) of 1-(2,2,2-trifluoroethoxy)naphthalene in Synthesis Example 1-3. With stirring, 2.2 g (0.0214 mol) of tetramethylene sulfoxide was added dropwise to the dispersion. The solution was matured overnight at room temperature and combined with 30 g of water and 30 g of diisopropyl ether, from which a water layer was separated. The water layer was again washed with 30 g of diisopropyl ether. This aqueous solution was combined with 3.4 g (0.0095 mol) of sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate synthesized in accordance with the teaching of JP-A 2007-145797, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water and distilled in vacuum to remove the solvent. The residue was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystals, 5.3 g, yield 87%.

後処理

  1. customin Synthesis Example 1-3
  2. customwas separated
  3. washThe water layer was again washed with 30 g of diisopropyl ether
  4. customsynthesized in accordance with the teaching of JP-A 2007-145797
  5. extractionafter which extraction
  6. washThe organic layer was washed with water
  7. distillationdistilled in vacuum
  8. customto remove the solvent
  9. additionThe residue was poured into isopropyl ether for crystallization
  10. filtrationfiltered
  11. customdried
  12. customobtaining the target compound

出典と根拠

ORDレコード
ord-0e40b955ab584c718cf2f0d8aaaec49c
出典データセット
uspto-grants-2013_12
特許番号
US08597869B2

関連ノート

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