Chloride → HCID 86695367, compound

HRID 1509377Notes

Reaction equation

HRID 1509377 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C1(C(O)=O)CCC=CC1.C(Cl)(=O)C(Cl)=O.[F:25][C:26]([F:37])([S:33]([O-:36])(=[O:35])=[O:34])[CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29].[C:38]1([S+:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C.[Cl-].Cl>C(Cl)Cl>[F:37][C:26]([F:25])([S:33]([O-:36])(=[O:34])=[O:35])[CH:27]([O:32][C:7]([CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:8])[C:28]([F:29])([F:31])[F:30].[C:51]1([S+:44]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

9

Reactant 7

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 209033-Cyclohexene-1-carboxylic acidHCID 65578Oxalyl chlorideHCID 5230583-Cyclohexene-1-carbonyl chloride2×HCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonate

Product 1

HCID 86695367HCID 86695367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Cyclohexenecarbonyl chloride prepared by reaction of 4.2 g (0.03 mole) of 3-cyclohexenecarboxylic acid with 5.1 g (0.04 mole) of oxalyl chloride was dissolved in 12 g of methylene chloride. A solution of 3-cyclohexenecarbonyl chloride in methylen chloride, as prepared above, was added dropwise to a mixed solution of 15 g (0.03 mole) of triphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonate prepared in accordance with the method described in Japanese Patent Laid-Open Publication No. 2007-145804, 2.4 g (24 millimoles) of triethylamine, 0.1 g (1 millimole) of N,N′-dimethylaminopyridine, and 60 g of methyle chloride. The mixture was then stirred at room temperature for 5 hours. After stirring, 30 g of 5% dilute hydrochloric acid was added to quench the reaction. An organic layer was isolated and washed with water. After washing with water, the organic layer was concentrated. To the organic layer, methyl isobutyl ketone was added, and the mixture was washed with water. After then, the washed organic layer was concentrated, and diisopropyl ether was added to perform recrystallization. The crystal was filtered off, collected, and dried under reduced pressure at 50° C. to obtain 14 g of triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-cyclohexenecarbonyloxy)propane-1-sulfonate (PAG intermediate) which was a target compound as a white crystal (yield: 78%).

Workup

  1. customprepared in accordance with the method
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. customAn organic layer was isolated
  6. washwashed with water
  7. washAfter washing with water
  8. concentrationthe organic layer was concentrated
  9. additionTo the organic layer, methyl isobutyl ketone was added
  10. washthe mixture was washed with water
  11. concentrationAfter then, the washed organic layer was concentrated
  12. additiondiisopropyl ether was added
  13. customrecrystallization
  14. filtrationThe crystal was filtered off
  15. customcollected
  16. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-e3984764144540daba6c461f01571b77
Source dataset
uspto-grants-2015_12
Patent number
US09223205B2

Reaction notes

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