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Potassium Phosphate, Tribasic → Methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate

HRID 2177344
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2177344
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH2:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][C:5]=2[C:7]([O:9][CH3:10])=[O:8])=[CH:23][CH:22]=1)[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 90418547Methyl 5-methyl-3-(((trifluoromethyl)sulfonyl)oxy)thiophene-2-carboxylate

Produkt 1

HCID 90418379Methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a 50-mL sealed tube (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed methyl 5-methyl-3-(((trifluoro methyl)sulfonyl)oxy)thiophene-2-carboxylate (1.7 g, 5.59 mmol), (4-ethylphenyl)boronic acid (1.0 g, 6.69 mmol), K3PO4 (3.84 g, 18.1 mmol), Pd(PPh3)4 (157 mg, 0.136 mmol), 1,4-dioxane (40 mL). The resulting solution was stirred overnight at 80° C. in an oil bath. The reaction progress was monitored by TLC/LCMS (ethyl acetate/petroleum ether=1:6). The solids were filtered out and washed by 20 mL ethyl acetate. Collected the organic phases and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 1.46 g (100%) of methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate as light yellow oil.

Aufarbeitung

  1. customInto a 50-mL sealed tube (1 atm)
  2. custompurged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. filtrationThe solids were filtered out
  5. washwashed by 20 mL ethyl acetate
  6. customCollected the organic phases
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 1.46 g (100%) of methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate as light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-43bdae2a1bef4e3c9dfba5f358638831
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067898B1

Notizen zur Reaktion

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