Tetramethylene sulfoxide → HCID 87825836, compound

HRID 1767431Notes

Reaction equation

HRID 1767431 reaction equation
[CH2:1]1[S:5](=O)[CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:8][CH2:9][CH3:10].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:41][C:42]([F:57])([S:53]([O-:56])(=[O:55])=[O:54])[C:43]([F:52])([F:51])[C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46].[K+]>ClCCl.C(OCC)C.O>[F:57][C:42]([F:41])([S:53]([O-:56])(=[O:55])=[O:54])[C:43]([F:51])([F:52])[C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46].[CH2:7]([O:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[S+:5]1[CH2:4][CH2:3][CH2:2][CH2:1]1)[CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 1128Tetramethylene sulfoxideHCID 82664Naphthalene, 2-butoxy-HCID 23675274Potassium perfluorobutanesulfonateHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 87825836HCID 87825836, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Next, 2.9 g (0.05 mol) of tetramethylene sulfoxide was added to 5.0 g (0.025 mol) of the 2-n-butoxynaphthalene and 15 g of Eaton's reagent (Aldrich), followed by 24 hours of stirring at room temperature. 200 g of water and 50 g of diethyl ether were added to the reaction mixture for separation into two layers. To the aqueous layer, 8.5 g (0.025 mol) of potassium perfluorobutanesulfonate and 100 g of dichloromethane were added, followed by one hour of stirring at room temperature. The organic layer separated was washed three times with 50 g of water, after which the solvent was evaporated off on a rotary evaporator. The oily matter was recrystallized from ethyl acetate, filtered and dried. There was obtained 13.8 g of the end compound, 2-n-butoxy-1-naphthyltetrahydrothiophenium perfluorobutanesulfonate (yield 94%).

Workup

  1. waitfollowed by one hour
  2. stirringof stirring at room temperature
  3. customThe organic layer separated
  4. washwas washed three times with 50 g of water
  5. customafter which the solvent was evaporated off on a rotary evaporator
  6. customThe oily matter was recrystallized from ethyl acetate
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-3e70d6adfeba43a3b449cac32285533e
Source dataset
uspto-grants-2007_06
Patent number
US07235343B2

Reaction notes

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