2'-Hydroxyacetophenone → (4-(Azetidine-1-carbonyl)phenyl)boronic acid

HRID 589028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589028
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCOC(C)=O>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 83752'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Produkt 1

HCID 13446028(4-(Azetidine-1-carbonyl)phenyl)boronic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(2-Hydroxyphenyl)ethanone (1.0 g, 7.3 mmol) and methyl bromoacetate (0.70 mL, 7.3 mmol) were combined in acetone (20.0 mL) with potassium carbonate (2.0 g, 15 mmol) and was stirred at room temperature. The reaction mixture was stirred for 18 h, diluted with EtOAc and filtered to remove the solids. The organic layer was concentrated to give the sub-title compound as a clear oil (1.5 g, 100%). LCMS calc. for C11H13O4 (M+H)+: m/z=209.1. found: 209.1.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 18 h
  2. filtrationfiltered
  3. customto remove the solids
  4. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-21872038f1a248b5942aa2794bd42f31
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227985B2

Notizen zur Reaktion

Wird geladen…