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Hydrochloric Acid → 4-Fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate

HRID 1506743
Notes
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Reaction equation

HRID 1506743 reaction equation
[C:1]12([CH:11]([OH:20])[C:12]([F:19])([F:18])[C:13]([O:15]CC)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].Cl.[Cl-].[F:25][C:26]1[CH:31]=[CH:30][C:29]([S+:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1>C(Cl)Cl.O.O1CCOCC1>[C:1]12([CH:11]([OH:20])[C:12]([F:19])([F:18])[C:13]([O-:15])=[O:14])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2.[F:25][C:26]1[CH:31]=[CH:30][C:29]([S+:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866496604-Fluorophenyldiphenylsulfonium chlorideHCID 117966659Ethyl 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate

Product 1

HCID 1317343644-Fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionateYield 57%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6.6 g of ethyl 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate, prepared in Synthesis Example 1-11, 50 g of 1,4-dioxane, 8.0 g of 25 wt % sodium hydroxide, and 20 g of water was stirred for 2 hours. To the reaction solution, 2.0 g of 35 wt % hydrochloric acid was added, and then 53 g of an aqueous solution of 4-fluorophenyldiphenylsulfonium 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 6.2 g of the target compound, 4-fluorophenyldiphenylsulfonium 3-(1-adamantyl)-2,2-difluoro-3-hydroxypropionate as white crystals (yield 57%).

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-6e9c65a5045c4f4c8000bac583fea248
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221742B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes