Tetramethylene sulfoxide → 4-(2-Methoxyethoxy)naphthalene 1-tetrahydrothiophenium 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropanesulfonate

HRID 2405633Notes

Reaction equation

HRID 2405633 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[CH2:16]1[S:20](=O)[CH2:19][CH2:18][CH2:17]1.C(OC(C)C)(C)C.[F:29][C:30]([F:53])([S:49]([O-:52])(=[O:51])=[O:50])[CH:31]([O:36][C:37]([C:39]12[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH2:40]1)[CH2:46]2)=[O:38])[C:32]([F:35])([F:34])[F:33].[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[C:39]12([C:37]([O:36][CH:31]([C:32]([F:35])([F:33])[F:34])[C:30]([F:29])([F:53])[S:49]([O-:52])(=[O:50])=[O:51])=[O:38])[CH2:40][CH:41]3[CH2:47][CH:45]([CH2:44][CH:43]([CH2:42]3)[CH2:48]1)[CH2:46]2.[SH+:20]1[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 1128Tetramethylene sulfoxideHCID 7914Diisopropyl EtherHCID 206591711-(2-Methoxyethoxy)naphthaleneHCID 86662327Sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate

Product 1

HCID 866623284-(2-Methoxyethoxy)naphthalene 1-tetrahydrothiophenium 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropanesulfonateYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Procedure

In 10 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 5.0 g (0.024 mol) of 1-(2-methoxyethoxy)naphthalene in Reference Synthesis Example 3. With stirring, 5.1 g (0.049 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 sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate (corresponding to 0.007 mol) synthesized according to the formulation described in JP-A 2007-145797, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water, and the solvent was distilled off in vacuum. The residue was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystal, 7.9 g, yield 94%.

Workup

  1. customin Reference Synthesis Example 3
  2. customwas separated
  3. washThe water layer was again washed with 30 g of diisopropyl ether
  4. customsynthesized
  5. extractionafter which extraction
  6. washThe organic layer was washed with water
  7. distillationthe solvent was distilled off in vacuum
  8. additionThe residue was poured into isopropyl ether for crystallization
  9. filtrationfiltered
  10. customdried
  11. customobtaining the target compound

Sources & evidence

ORD record
ord-b97c1899039649a0976e58341804cf0b
Source dataset
uspto-grants-2014_08
Patent number
US08808964B2

Reaction notes

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