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Cesium carbonate → HCID 69352826, Verbindung

HRID 348294
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348294
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:32]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:37]=[CH:36][CH:35]=[C:34]([C:38]2[O:39][C:40]([CH3:56])=[C:41]([CH2:43][CH2:44]OS(C3C=CC(C)=CC=3)(=O)=O)[N:42]=2)[CH:33]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:44][CH2:43][C:41]2[N:42]=[C:38]([C:34]3[CH:33]=[C:32]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[CH:37]=[CH:36][CH:35]=3)[O:39][C:40]=2[CH3:56])=[C:9]([CH2:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 208231533-(4-Hydroxy-3-propylphenyl)-2-methyl-2-phenoxy-propionic Acid Ethyl EsterHCID 58979436Toluene-4-sulfonic acid 2-(2-biphenyl-3-yl-5-methyloxazol-4-yl)ethyl ester

Produkt 1

HCID 69352826HCID 69352826, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of 3-(4-hydroxy-3-propylphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (266 mg, 1.0 mmol) in DMF (10 mL) was treated with cesium carbonate (407 mg, 1.25 mmol) and toluene-4-sulfonic acid 2-(2-biphenyl-3-yl-5-methyl-oxazol-4-yl)-ethyl ester (520 mg, 1.20 mmol) (see Ex. 2, Part F) and then heated at 55° C. for 18 h. After cooling to ambient temperature, the mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and then the organic phases were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetatelhexanes) to provide the desired product (315 mg, 60%) as a clear, colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.68–7.63 (m, 3H), 7.51 (t, J=7.6 Hz, 1H), 7.46 (t, J=8.0 Hz, 2H), 7.38 (t, J=7.2 Hz, 1H), 7.25–7.21 (m, 2H), 7.04–6.96 (m, 3H), 6.85–6.69 (m, 3H), 4.26 (t, J=6.4 Hz, 2H), 4.21 (q, J=6.8 Hz, 2H), 3.26 (A of AB, J=13.6 Hz, 1H), 3.09 (B of AB, J=13.6 Hz, 1H), 3.01 (t, J=6.4 Hz, 2H), 2.54 (t, J=7.6 Hz, 2H), 2.41 (s, 3H), 1.54 (sextet, J=7.6 Hz, 2H), 1.41 (s, 3H), 1.23 (t, J=6.8 Hz, 3H), 0.91 (t, J=7.2 Hz, 3H); MS (EI) 604.3 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetatelhexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ba86ed87d2f644eab28058572c2282da
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176224B2

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