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

Potassium Carbonate → 3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(3,4-dimethyl-phenoxy)-2-methyl-propionic acid

HRID 348335
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348335
C(OC(=O)[C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1)([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH3:25][C:26]1[O:30][C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[N:28][C:27]=1[CH2:43][CH2:44]OS(C1C=CC(C)=CC=1)(=O)=O.[C:56]([O-:59])([O-])=[O:57].[K+].[K+].[OH-].[Na+]>C(O)C>[C:34]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:35]=[CH:36][C:31]([C:29]2[O:30][C:26]([CH3:25])=[C:27]([CH2:43][CH2:44][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C:5]([O:15][C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=4)([CH3:14])[C:56]([OH:59])=[O:57])=[CH:12][CH:11]=3)[N:28]=2)=[CH:32][CH:33]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 693170842-(3,4-Dimethylphenoxy)-3-(4-hydroxyphenyl)-2-methylpropionic acid ethyl ester

Produkt 1

HCID 10144341
3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(3,4-dimethyl-phenoxy)-2-methyl-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of 2-(3,4-dimethylphenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol) (see Ex. 32, Part C), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 1, Part I) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 3-{4-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(3,4-dimethyl-phenoxy)-2-methyl-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, 2H, J=8.4 Hz), 7.71 (d, 2H, J=8.4 Hz), 7.65–7.62 (m, 2H), 7.49–7.45 (m, 2H), 7.42–7.30 (m, 1H), 7.19 (d, 2H, J=8.4 Hz), 7.00 (d, 1H, J=8.4 Hz), 6.83 (d, 2H, J=8.4 Hz), 6.70 (d, 1H, J=2.4 Hz), 6.64 (dd, 1H, J=8.4, 2.4 Hz), 4.26 (t, 2H, J=6.0 Hz), 3.22 and 3.11 (d of Abq, 2H, J=14.0 Hz), 3.09 (t, 2H, J=6.0 Hz), 2.44 (s, 3H), 2.19 (s, 3H), 2.18 (s, 3H), 1.39 (s, 3H). IR (KBr) 3480, 2950, 1718, 1611, 1512, 1248, 1177 cm−1. HRMS (ES+) m/z exact mass calcd for C36H36NO5 562.2593, found 562.2595.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 24 h under N2
  3. temperaturewas heated
  4. temperatureat reflux for an additional 2 h
  5. temperatureThe reaction was cooled
  6. customthe solvent removed in vacuo
  7. extractionextracted with water and CH2Cl2
  8. customthe organic layer dried
  9. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-04a09f94b98f4b3c9b0cce15725565b1
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