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

HRID 1443744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443744
[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-81a8ec246f8543febac4ed3f38d0126c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662771B2

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