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

HRID 1907084Notes

Reaction equation

HRID 1907084 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-269eae129adf4d518aece073aea0696f
Source dataset
uspto-grants-2013_12
Patent number
US08597869B2

Reaction notes

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