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1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane → HCID 178494055, Verbindung

HRID 633595
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 633595
Br[C:2]1[CH:17]=[C:16]([S:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1.C[C:27]12CC3(C)P(C4C=CC=CC=4)[C:33](C)([CH2:35][C:29]([CH3:45])(O3)O1)[O:34]2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:27][O:34][C:33]1[N:11]=[CH:8][CH:7]=[C:29]2[C:45]([C:2]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=3[O:4][C@H:5]3[CH2:10][CH2:9][C@H:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]3)=[CH:22][N:21]([CH3:25])[C:35]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 534277901,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantaneHCID 178484115HCID 178484115, Verbindung

Produkt 1

HCID 178494055HCID 178494055, VerbindungAusbeute 341,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of Example 144B (60 mg, 0.14 mmol) and Example 59A (40.1 mg, 0.14 mmol) was degassed under argon. To this mixture was added dioxane (8 mL) followed by degassing with argon. To this mixture was added potassium phosphate, dibasic (109 mg, 0.626 mmol) and water (2.000 mL) followed by degassing with argon. To this mixture was added 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (6.91 mg, 0.024 mmol) and then immediately tris(dibenzylideneacetone)dipalladium (0) (8.92 mg, 9.74 μmol) followed by degassing with argon. The reaction mixture was heated at 100° C. for 1 hour. The mixture was cooled to ambient temperature and partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated to provide the title compound (0.042 g, 59% yield)

Aufarbeitung

  1. customby degassing with argon
  2. additionTo this mixture was added potassium phosphate, dibasic (109 mg, 0.626 mmol) and water (2.000 mL)
  3. customby degassing with argon
  4. customby degassing with argon
  5. temperatureThe mixture was cooled to ambient temperature
  6. custompartitioned between saturated aqueous sodium chloride and ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3b156b009b74979a593bb0e8ca551bd
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321764B2

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