Carbon tetrabromide → Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoate

HRID 1039154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039154
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:21])[NH:11][CH2:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:21][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:11]=1

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 59167774HCID 59167774, Verbindung

Produkt 1

HCID 59167750Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoateAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Add a solution of 7-(2-oxo-2-phenylethylcarbamoyl)heptanoic acid methyl ester (7.05 g, 23.1 mmol) and carbon tetrabromide (11.3 g, 34.3 mmol) in methylene chloride over 40 minutes to a mixture of triphenylphosphine (9.0 g, 34.3 mmol) and DMAP (5.51 g, 45.1 mmol) in methylene chloride (500 mL) at room temperature under nitrogen. Stir the mixture for 30 minutes and add additional triphenylphosphine (2.6 g, 9.92 mmol) and carbon tetrabromide (3.35 g, 10.1 mmol). Stir the mixture for an additional 20 minutes, filter through Celite and wash with ethyl acetate (3×100 mL). Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (70:30), to provide 7-(5-phenyloxazol-2-yl)heptanoic acid methyl ester (2.75 g, 41%).

Aufarbeitung

  1. stirringStir the mixture for an additional 20 minutes
  2. filtrationfilter through Celite
  3. washwash with ethyl acetate (3×100 mL)
  4. customRemove the solvent under reduced pressure
  5. custompurify the residue by flash column chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate (70:30)

Quellen und Nachweise

ORD-Eintrag
ord-3ae180d21ed1473a93b9e77a7250a9ab
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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