Water → tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480686
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O>CN(C)C=O>[CH2:12]([O:11][C:9]([CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:10])[CH:13]=[CH2:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 18766560Allyl 3-hydroxyphenylacetate

Produkt 1

HCID 18766493tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Allyl 3-hydroxyphenylacetate (2.64 g, 13.7 mmol), potassium carbonate (3.79 g, 27.4 mmol), and tert-butyl 2-bromoisobutyrate (7.65 g, 34.3 mmol) were dissolved in dimethylformamide (5 mL), and the mixture was stirred for 13 hours at 80° C. The reaction mixture was added to water, and the resultant mixture was extracted with diethyl ether. Washing was performed sequentially with water and saturated brine, followed by drying over magnesium sulfate. The mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound was obtained (3.47 g, 10.38 mmol, 75.7%).

Aufarbeitung

  1. extractionthe resultant mixture was extracted with diethyl ether
  2. washWashing
  3. dry with materialby drying over magnesium sulfate
  4. concentrationThe mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound
  5. customwas obtained (3.47 g, 10.38 mmol, 75.7%)

Quellen und Nachweise

ORD-Eintrag
ord-e4bb55fcf7314091838a119632fd7785
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653334B1

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