Triethylamine → [3-Bromo-4-(t-butyldimethyl-silanyloxy)-5-methoxy-phenyl]-acetic acid methyl ester

HRID 547140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547140
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][O:24][C:25](=[O:37])[CH2:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30](O)=[C:29]([Br:36])[CH:28]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:23][O:24][C:25](=[O:37])[CH2:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:29]([Br:36])[CH:28]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 57443577(3-bromo-4-hydroxy-5-methoxy-phenyl)-acetic Acid Methyl Ester

Produkt 1

HCID 57709032[3-Bromo-4-(t-butyldimethyl-silanyloxy)-5-methoxy-phenyl]-acetic acid methyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic acid t-butyldimethylsilyl ester (0.159 mL, 0.690 mmol) and triethylamine (0.120 mL, 0.863 mmol) were added to a solution of (3-bromo-4-hydroxy-5-methoxy-phenyl)-acetic acid methyl ester (158 mg, 0.574 mmol) in dichloromethane (4 mL), and the mixture was stirred at room temperature for one hour. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50) to give the target compound as a colorless oil (203 mg, 91%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-41f8811a33d048bcafd008e8924d0c9c
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

Notizen zur Reaktion

Wird geladen…