Tetramethylene sulfoxide → 4-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate

HRID 1907084ノート

反応式

HRID 1907084 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.[F:30][C:31]([F:55])([S:51]([O-:54])(=[O:53])=[O:52])[CH:32]([O:37][C:38]([C:40]12[CH2:49][CH:44]3[CH2:45][CH:46]([CH2:48][CH:42]([C:43]3=[O:50])[CH2:41]1)[CH2:47]2)=[O:39])[C:33]([F:36])([F:35])[F:34].C([NH+](CC)CC)C>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>[F:55][C:31]([F:30])([S:51]([O-:54])(=[O:52])=[O:53])[CH:32]([O:37][C:38]([C:40]12[CH2:49][CH:44]3[CH2:45][CH:46]([CH2:48][CH:42]([C:43]3=[O:50])[CH2:41]1)[CH2:47]2)=[O:39])[C:33]([F:34])([F:36])[F:35].[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 134430561-(2,2,2-Trifluoroethoxy)naphthaleneHCID 86664296Triethylammonium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate

生成物 1

HCID 866642954-(2,2,2-Trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate収率 84%

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 an aqueous solution of triethylammonium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate (corresponding to 0.0086 mol) synthesized in accordance with the teaching of JP-A 2008-106045, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water, distilled in vacuum to remove the solvent, and dried, obtaining the target compound. Amorphous solids, 5.2 g, yield 84%.

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 2008-106045
  5. extractionafter which extraction
  6. washThe organic layer was washed with water
  7. distillationdistilled in vacuum
  8. customto remove the solvent
  9. customdried
  10. customobtaining the target compound

出典と根拠

ORDレコード
ord-269eae129adf4d518aece073aea0696f
出典データセット
uspto-grants-2013_12
特許番号
US08597869B2

反応ノート

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