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Hydrochloric Acid → 3-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

HRID 1993033
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1993033
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14].[CH2:25]([O:27][C:28](=[O:41])[CH2:29][CH:30]([C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[C:31]#[C:32][CH3:33])[CH3:26].Cl>CN(C=O)C.O>[CH2:25]([O:27][C:28](=[O:41])[CH2:29][CH:30]([C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:38][CH:39]=1)[C:31]#[C:32][CH3:33])[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazoleHCID 59132733Ethyl 3-(4-hydroxyphenyl)hex-4-ynoate

Produkt 1

HCID 591326383-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Cesium carbonate (0.51 g, 1.57 mmol) was added to a solution of 18.2 (216 mg, 0.79 mmol) and phenol 16 (220 mg, 0.79 mmol) in DMF (8 mL). The reaction was stirred at room temperature overnight and then taken up in water (500 mL). The solution was adjusted to pH=4.0 with 1N HCl(aq) and extracted with ethyl acetate (2×25 mL). The combined organics were washed with water, followed by brine. The solvent was removed under reduced pressure and the resulting residue was purified via radial chromatography (20% diethyl ether in hexanes) to yield 304 mg (82%) of 3-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester. LC/MSD m/e: 472.0 (M+H); 1H NMR (400 MHz) (CDCl3) δ 8.16 (2H, d, J=8.0 Hz), 7.73 (2H, d, J=8.0 Hz), 7.33 (2H, m), 6.99 (2H, m), 5.01 (2H, s), 4.14 (3H, m), 2.72 (2H, m), 2.48 (3H, s), 1.85 (3H, s), 1.26 (3H, t, J=8.0 Hz).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. washThe combined organics were washed with water
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was purified via radial chromatography (20% diethyl ether in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3422f5665d9e40caac72148b944f5149
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07649110B2

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