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Sodium Iodide → (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

HRID 2387301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387301
[F:1][C:2]([F:28])([F:27])[C@@:3]([CH2:17][S@:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=O)([OH:16])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH3:15])([CH3:7])[CH3:6].[I-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC(C)=O>[F:28][C:2]([F:1])([F:27])[C@@:3]([CH2:17][S:18][C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)([OH:16])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH3:15])([CH3:6])[CH3:7]
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Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 58933190(S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol

Produkt 1

HCID 58933188(S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-olAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel
2×

Versuchsvorschrift

To a suspension of (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol (31.9 g, 76.6 mmol) and sodium iodide (34.4 g, 230 mmol) in 450 mL of anhydrous acetone at −40° C. was added a solution of trifluoroacetic acid anhydride (54.1 mL, 383 mmol) in 200 mL of anhydrous acetone via an addition funnel dropwise over 30 minutes. A greenish brown mixture formed instantaneously. After 15 minutes, the reaction mixture was quenched by slow addition of saturated aqueous sodium sulfite solution and neutralized with saturated aqueous sodium carbonate solution. The mixture became colorless and was concentrated in vacuo to remove most of the acetone solvent. The resulting material was diluted with 400 mL of water and extracted with three 400 mL portions of diethyl ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol as a yellow oil (31.0 g, 100%).

Aufarbeitung

  1. customA greenish brown mixture formed instantaneously
  2. customthe reaction mixture was quenched by slow addition of saturated aqueous sodium sulfite solution
  3. concentrationwas concentrated in vacuo
  4. customto remove most of the acetone solvent
  5. additionThe resulting material was diluted with 400 mL of water
  6. extractionextracted with three 400 mL portions of diethyl ether
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d36f33826fdc4aaa92c1fc8033c5be5e
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268859B2

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