Sodium Iodide → (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

HRID 854172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854172
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:30])([CH3:29])[CH2:12][C@:13]([CH2:19][S@:20]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=O)([OH:18])[C:14]([F:17])([F:16])[F:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[I-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:30])([CH3:29])[CH2:12][C@:13]([CH2:19][S:20][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)([OH:18])[C:14]([F:17])([F:15])[F:16])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 69416652(S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol

Produkt 1

HCID 69415185(S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-olAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a suspension of (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol (11.5 g, 22.8 mmol) and sodium iodide (10.2 g, 68.1 mmol) in 180 mL of anhydrous acetone at −40° C. was added a solution of trifluoroacetic acid anhydride (16.0 mL, 113 mmol) in 30 mL of anhydrous acetone dropwise by syringe over 20 minutes. A greenish brown mixture was formed instantaneously. After 20 minutes, the reaction mixture was quenched with saturated aqueous sodium sulfite solution and neutralized with saturated aqueous sodium carbonate solution. The brown color disappeared and the crude was concentrated to remove most of the acetone solvent. The resulting material was diluted with 350 mL of water and extracted with three 600 mL portions of ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethyl-pentan-2-ol as a yellow oil (11.1 g, 99%).

Aufarbeitung

  1. customA greenish brown mixture was formed instantaneously
  2. customthe reaction mixture was quenched with saturated aqueous sodium sulfite solution
  3. concentrationthe crude was concentrated
  4. customto remove most of the acetone solvent
  5. additionThe resulting material was diluted with 350 mL of water
  6. extractionextracted with three 600 mL portions of 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-b7aa1f4da056454fbd5c81aea55bbaa3
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256300B2

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