Boron tribromide → 5-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1039246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039246
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[N:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:12]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 591677855-[4-(2-Methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

Produkt 1

HCID 684911055-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dissolve 5-[4-(2-methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (3.5 g, 11.5 mmol) in CH2Cl2 (50 mL) under nitrogen at RT. Add boron tribromide (1M in CH2Cl2, 29 mL) and stir at RT until the reaction is complete. Quench the mixture into ice/water and extract with CH2Cl2. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) to allow for isolation of 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (2.61 g, 78%). MS (ES): (M+1)+ 290.2 m/z.

Aufarbeitung

  1. customQuench the mixture into ice/water
  2. extractionextract with CH2Cl2
  3. dry with materialDry the combined extracts over Na2SO4
  4. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-f4c35f20be0f4bfc99b013cfe0ff830b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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