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Sodium Iodide → tert-Butyl 4-[(1R)-3-iodo-1-phenylpropoxy]-3-methylphenyl carbonate

HRID 131757
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 131757
Cl[CH2:2][CH2:3][C@H:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][C:7]=1[CH3:20].[I-:27].[Na+].CC(=O)CC>CCOCC>[I:27][CH2:2][CH2:3][C@H:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][C:7]=1[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 29976195(R)-3-Chloro-1-phenyl-1-[2-methyl-4-[(tert-butoxycarbonyl)oxy]phenoxy]propane

Produkt 1

HCID 69118199tert-Butyl 4-[(1R)-3-iodo-1-phenylpropoxy]-3-methylphenyl carbonateAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl Ether
Lösungsmittel

Versuchsvorschrift

A dry 1-L R.B. flask was charged (R)-3-chloro-1-phenyl-1-(2-methyl-4-((tert-butoxycarbonyl)oxy)phenoxy)propane (18.00 g, 47.80 mmol), sodium iodide (90.0 g, 600 mmol) and 2-butanone (550 mL). The reaction flask was protected from light. The reaction mixture was stirred at reflux temperature under nitrogen for 16 hours. The mixture was cooled to room temperature and poured into ether (1 L). The insoluble inorganic salts (white precipitate) were removed by filtration. The filtrate was concentrated under reduced pressure and the crude residue was dissolved in diethyl ether (1 L). The ethereal layer was washed with cold saturated sodium bisulfite solution (2×200 mL), water and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to flash chromatography, eluting with 20% ethyl acetate in hexane to provide 20.5 grams (91%) of the desired compound.

Aufarbeitung

  1. temperatureat reflux temperature under nitrogen for 16 hours
  2. customThe insoluble inorganic salts (white precipitate) were removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe crude residue was dissolved in diethyl ether (1 L)
  5. washThe ethereal layer was washed with cold saturated sodium bisulfite solution (2×200 mL), water and saturated aqueous sodium chloride
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f8f8f2e53426433f9c0cddee1ed9813a
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07384983B2

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