Hydrochloric Acid → Triphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate

HRID 1506740Notes

Reaction equation

HRID 1506740 reaction equation
[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:15]2[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:17][CH:9]1[CH2:10]3)[CH2:14]2)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl.[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>C(Cl)Cl.O1CCOCC1>[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:9]2[CH2:17][CH:13]3[CH2:12][CH:11]([CH2:16][CH:15]1[CH2:14]3)[CH2:10]2)[C:3]([O-:5])=[O:4].[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61343Triphenylsulfonium chlorideHCID 117966647Ethyl difluoro-(2-hydroxy-adamantan-2-yl)acetate

Product 1

HCID 131734362Triphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetateYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.9 g of ethyl difluoro-(2-hydroxyadamantan-2-yl)acetate, prepared in Synthesis Example 1-8, 20 g of 1,4-dioxane, and 4.8 g of 25 wt % sodium hydroxide was stirred for 2 hours. To the reaction solution, 1.5 g of 35 wt % hydrochloric acid was added, and then 24 g of an aqueous solution of triphenylsulfonium chloride and 100 g of methylene chloride were added. After stirring for 30 minutes, the organic layer was taken out, washed with water, and concentrated under reduced pressure. Methyl isobutyl ketone was added to the concentrate, which was concentrated again. Diisopropyl ether was added to the concentrate for crystallization. The resulting solid was dried in vacuum, obtaining 4.7 g of the target compound, triphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate as white crystals (yield 63%).

Workup

  1. stirringAfter stirring for 30 minutes
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. additionMethyl isobutyl ketone was added to the concentrate, which
  5. concentrationwas concentrated again
  6. additionDiisopropyl ether was added to the
  7. concentrationconcentrate for crystallization
  8. customThe resulting solid was dried in vacuum

Sources & evidence

ORD record
ord-5c7799e9780446cc91700756c58787d9
Source dataset
uspto-grants-2015_12
Patent number
US09221742B2

Reaction notes

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