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

Water → Methyl 5-[(4-ethylphenyl)methyl]-3-hydroxy-2-naphthoate

HRID 221945
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 221945
[OH:1][C:2]1[C:3]([C:20]([O:22][CH3:23])=[O:21])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9](OS(C(F)(F)F)(=O)=O)[CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1.[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH2:9]([C:10]1[CH:11]=[CH:2][C:3]([CH2:20][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH:11]=[C:2]([OH:1])[C:3]([C:20]([O:22][CH3:23])=[O:21])=[CH:4]3)=[CH:4][CH:5]=1)[CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962Water2×HCID 10796Cesium carbonateHCID 59488801Methyl 3-hydroxy-5-trifluoromethanesulfonyloxy-2-naphthoate

Produkt 1

HCID 59488750Methyl 5-[(4-ethylphenyl)methyl]-3-hydroxy-2-naphthoateAusbeute 151,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479793
cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under a nitrogen stream, the known compound methyl 3-hydroxy-5-trifluoromethanesulfonyloxy-2-naphthoate (Bull. Korean Chem. Soc. 2000, 21, 757; 82.3 mg, 0.23 mmol), diphenylphosphino ferrocene palladium dichloride (17.3 mg, 0.021 mmol), 2-[(4-ethylphenyl)methyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborane (57.8 mg, 0.24 mmol) and cesium carbonate (228.6 mg, 0.70 mmol) were dissolved in tetrahydrofuran (2.0 mL). Water (0.2 mL) was added thereto, and then the mixture was stirred for 30 minutes at 100° C. in a microwave apparatus. Water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:20)), to thereby obtain the titled compound (55.8 mg, 74%).

Aufarbeitung

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:20))

Quellen und Nachweise

ORD-Eintrag
ord-234646172ba64e6b8bea8366d40eefeb
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08207134B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion