StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Carbonate → 2-(4-Thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol

HRID 348276
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348276
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27339602-Thiopheneboronic acidHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

Produkt 1

HCID 210842832-(4-Thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2-(4-Bromophenyl)-5-methyl-4-oxazoleethanol (10.0 g, 35.0 mmol) (see Ex. 1, Part G) and 2-thiophenyl boronic acid (38.0 mmol) were dissolved in n-propanol (120 ml) before adding triphenylphosphine (165.2 mg, 0.63 mmol), palladium acetate (46 mg, 2.1 mmol), and Na2CO3 (4.5 g, 42 mmol dissolved in 30 mL distilled H2O). The solution was heated to reflux and stirred for 1.5 h. After cooling to ambient temperature, the mixture was concentrated under reduced pressure and then partitioned between CH2Cl2 (100 mL) and 1N NaOH (100 mL). The aqueous phase was extracted with CH2Cl2 (2×50 mL) and the combined organic phases were dried (MgSO4) and concentrated under reduced pressure to provide 2-(4-thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompartitioned between CH2Cl2 (100 mL) and 1N NaOH (100 mL)
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e73865833f949b8aab027a622d371b5
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176224B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion