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Potassium Phosphate, Tribasic → Methyl 3-benzyloxy-5-phenylbenzoate

HRID 1096948
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096948
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:33]=[C:34](OS(C(F)(F)F)(=O)=O)[CH:35]=1)[C:29]([O:31][CH3:32])=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([C:29]([O:31][CH3:32])=[O:30])[CH:33]=[C:34]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:35]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoate

Produkt 1

HCID 18945315Methyl 3-benzyloxy-5-phenylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Phenylboronic acid (1.2 g), Pd(PPh3)4 (364 mg) and potassium phosphate (4 g) were added in that order to a DME (60 mL) solution of methyl 3-benzyloxy-5-{[(trifluoromethyl)sulfonyl]-oxy}benzoate (2.5 g), and stirred at 85° C. for 7 hours. The reaction liquid was filtered through Celite, concentrated under reduced pressure, and the residue was diluted with ethyl acetate, water was added to it, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a colorless oil.

Aufarbeitung

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate, water
  5. additionwas added to it
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-efe18fbcd3814819bf60a783ea75708d
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138197B2

Notizen zur Reaktion

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