Hydrochloric Acid → HCID 86642238, compound

HRID 1943570Notes

Reaction equation

HRID 1943570 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([O-:8])(=[O:7])=[O:6].[C:9]1([S+:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[C:35]12([C:45](Cl)=[O:46])[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43][CH:37]([CH2:38]3)[CH2:36]1)[CH2:42]2.Cl>C(Cl)Cl>[C:35]12([C:45]([O:1][CH2:2][CH2:3][CH2:4][S:5]([O-:8])(=[O:7])=[O:6])=[O:46])[CH2:42][CH:41]3[CH2:40][CH:39]([CH2:38][CH:37]([CH2:43]3)[CH2:36]1)[CH2:44]2.[C:22]1([S+:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 86642237HCID 86642237, compound

Product 1

HCID 86642238HCID 86642238, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2.1 g (5 mmol) of the triphenylsulfonium 3-hydroxypropanesulfonate prepared in Synthesis Example 1-14, 0.6 g (6 mmol) of triethylamine and 10 g of methylene chloride, 2.9 g (6 mmol) of 1-adamantanecarbonyl chloride was added dropwise, followed by stirring for 3 hours at room temperature. Then 5.5 g of 5% aqueous hydrochloric acid was added to quench the reaction. The organic layer was separated from the reaction solution, washed with water, and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while azeotroping off the residual water. Diisopropyl ether was added to the residue, followed by decantation and drying. There was obtained the target compound, triphenylsulfonium 3-(adamantane-1-carbonyloxy)propanesulfonate. Colorless oily matter, 2.3 g, yield 79%. The compound, designated PAG-5, has the following structure.

Workup

  1. additionwas added dropwise
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated from the reaction solution
  5. washwashed with water
  6. concentrationconcentrated in vacuum
  7. additionMethyl isobutyl ketone was added to the concentrate, which
  8. concentrationwas concentrated in vacuum again
  9. customwhile azeotroping off the residual water
  10. additionDiisopropyl ether was added to the residue
  11. customdrying

Sources & evidence

ORD record
ord-654d25327572426bb82ff5738e587608
Source dataset
uspto-grants-2013_03
Patent number
US08394570B2

Reaction notes

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