Hydrochloric Acid → [4-(1-Hydroxycyclopropyl)phenyl]boronic acid

HRID 502858

Reaktionsgleichung

Reaktionsgleichung von HRID 502858
[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:23])[C:8]1[CH:13]=[CH:12][C:11]([B:14]2[O:18]C(C)(C)C(C)(C)[O:15]2)=[CH:10][CH:9]=1.Cl>C(OCC)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[OH:23][C:7]1([C:8]2[CH:9]=[CH:10][C:11]([B:14]([OH:15])[OH:18])=[CH:12][CH:13]=2)[CH2:2][CH2:1]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 57416393[4-(1-Hydroxycyclopropyl)phenyl]boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 3.0 M solution of ethylmagnesium bromide in diethylether (7.6 mL) is added to a stirred solution of titanium(IV) isopropoxide (2.2 mL) in diethylether (70 mL) chilled to −78° C. The resultant solution is stirred at −78° C. for 1.5 h, before 4-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-benzoic acid methyl ester (2.0 g) is added. The reaction mixture is warmed to ambient temperature and stirred for an additional 12 h. Then, 1 M aqueous hydrochloric acid is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The residue is dissolved in acetone (60 mL) and 0.1 M aqueous NH4OAc solution (50 mL) followed by NalO4 (2.3 g) is added. The resulting reaction mixture is stirred at room temperature for 18 h. After removal of the acetone, the residue is extracted with ethyl acetate. The combined extracts are dried (sodium sulphate) and the solvent is evaporated. The residue is purified by chromatography on silicagel (cyclohexane/ethyl acetate).

Aufarbeitung

  1. additionis added
  2. temperatureThe reaction mixture is warmed to ambient temperature
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried (sodium sulphate)
  5. customthe solvent is evaporated
  6. dissolutionThe residue is dissolved in acetone (60 mL)
  7. additionis added
  8. customThe resulting reaction mixture
  9. stirringis stirred at room temperature for 18 h
  10. customAfter removal of the acetone
  11. extractionthe residue is extracted with ethyl acetate
  12. dry with materialThe combined extracts are dried (sodium sulphate)
  13. customthe solvent is evaporated
  14. customThe residue is purified by chromatography on silicagel (cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c056499d41ec42609bb9c55e3547a795
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776830B2

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