Cesium carbonate → HCID 11025958, Verbindung

HRID 898415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898415
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.[CH2:26]([O:28][C:29](=[O:41])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1)([CH3:32])[CH3:31])[CH3:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:26]([O:28][C:29](=[O:41])[C:30]([CH3:32])([O:33][C:34]1[CH:39]=[CH:38][C:37]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][CH:35]=1)[CH3:31])[CH3:27]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 11025958HCID 11025958, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester (See Japan Tobacco Inc International Application WO 9518125) (24 g, 66.9 mmol), 2-(4-hydroxyphenoxy)-2-methylpropanoic acid ethyl ester (See American Home Products U.S. Pat. No. 3,795,691) (12.5 g, 55.71 mmol) and Cs2CO3 (22.7 g, 69.6 mmol) was heated at 55° C. in DMF (45 mL) for 18 h. The reaction was partitioned between EtOAc (160 mL) and H2O (180 mL), and the aqueous phase extracted with EtOAc (150 mL). The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to an oil which was purified by column chromatography (1500 mL SiO2, 10% EtOAc/hexanes to 20% EtOAc/hexanes) to provide 2-methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid ethyl ester (17.8 g, 78%) as a colorless, viscous oil: Rf=0.48 in 35% EtOAc/hexanes; 1H NMR (400 MHz, CDCl3) δ 7.99-7.96 (m, 2H), 7.43-7.40 (m, 3H), 6.83-6.75 (m, 4H), 4.22 (q, J=9.2 Hz, 2H), 4.18 (t, J=8.8 Hz, 2H), 2.95 (t, J=8.8 Hz, 2H), 2.36 (s, 3H), 1.52 (s, 6H), 1.27 (t, J=9.2 Hz, 3H).

Aufarbeitung

  1. customThe reaction was partitioned between EtOAc (160 mL) and H2O (180 mL)
  2. extractionthe aqueous phase extracted with EtOAc (150 mL)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure to an oil which
  5. customwas purified by column chromatography (1500 mL SiO2, 10% EtOAc/hexanes to 20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-febb5b20b298472ca551c157a2531b96
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351728B2

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