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Water → 5-(4,4,5,5,5-Pentafluoropentylsulfinyl)pentanal

HRID 1792333
Notes
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Reaction equation

HRID 1792333 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][CH2:7][S:8]([CH2:10][CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[O:9].C(O)(C(F)(F)F)=O.O.CCCCCC>C(Cl)(Cl)Cl.C(OCC)(=O)C>[F:19][C:13]([F:18])([C:14]([F:15])([F:16])[F:17])[CH2:12][CH2:11][CH2:10][S:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[O:2])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 22033402HCID 22033402, compound

Product 1

HCID 220333425-(4,4,5,5,5-Pentafluoropentylsulfinyl)pentanalYield 95.1%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

5,5-Dimethoxy-1-(4,4,5,5,5-pentafluoropentylsulfinyl)pentane (355 mg, 0.10 mmol) was dissolved in chloroform (2 ml), 50% TFA aqueous solution (2 ml) was added thereto at room temperature, and the resulting mixture was then stirred for 2 hours. After the reaction was completed, the reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1-ethyl acetate) to give 5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentanal (28 mg, yield 93%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-c82084f26390484a87066af56670b886
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074819B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes