Triphenylsulfonium chloride → HCID 21111909, compound

HRID 558047Notes

Reaction equation

HRID 558047 reaction equation
[Na].[O:2]=[C:3]1[CH:10]2[CH2:11][C:6]3([O:13][C:14](=[O:22])[C:15]([F:21])([F:20])[S:16]([OH:19])(=[O:18])=[O:17])[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[Cl-].[C:24]1([S+:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.C(#N)C>[O:2]=[C:3]1[CH:10]2[CH2:11][C:6]3([O:13][C:14]([C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:17])=[O:18])=[O:22])[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:37]1([S+:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 61343Triphenylsulfonium chlorideHCID 5360545SodiumHCID 21111910HCID 21111910, compound

Product 1

HCID 21111909HCID 21111909, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

To 5.4 parts (35.6% purity) of the sodium salt of difluorosulfoacetic acid-4-oxo-1-adamantyl ester, a mixture of 16 parts of acetonitrile and 16 parts of ion-exchanged water was added. To the mixture, a solution of 1.7 parts of triphenylsulfonium chloride, 5 parts of acetonitrile, and 5 parts of ion-exchanged water was added. The resultant mixture was stirred for 15 hours, then concentrated, and extracted with 142 parts of chloroform. The organic layer was washed with ion-exchanged water, and the resulting organic layer was concentrated. The concentrate was washed with 24 parts of tert-butyl methyl ether, giving 1.7 parts of triphenylsulfonium 4-oxo-1-adamantyloxycarbonyldifluromethanesulfonate (B1) in the form of a white solid.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. extractionextracted with 142 parts of chloroform
  4. washThe organic layer was washed with ion-exchanged water
  5. concentrationthe resulting organic layer was concentrated
  6. washThe concentrate was washed with 24 parts of tert-butyl methyl ether

Sources & evidence

ORD record
ord-52101f50f7df40af94e977c8e065c0bf
Source dataset
uspto-grants-2011_11
Patent number
US08062829B2

Reaction notes

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