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Dimethylformamide → Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

HRID 530929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 530929
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CN(C)C=O.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:24][CH:23]=1>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:27][CH:26]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Produkt 1

HCID 68357704Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

Potassium carbonate (1.38 g) and tert-butyl bromoacetate (1.07 g) were added to a dehydrated N,N-dimethylformamide (17 mL) solution of benzyl (4-hydroxyphenyl)acetate (1.21 g) at room temperature, followed by stirring for 1 hour. Thereafter, water was added to the reaction mixture on an ice bath, and extraction was performed with hexane:ethyl acetate=2:1. The resulting organic phase was washed with an aqueous saturated sodium chloride solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2) to obtain the title compound (1.75 g) having the following physical property values.

Aufarbeitung

  1. extractionextraction
  2. washThe resulting organic phase was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2)

Quellen und Nachweise

ORD-Eintrag
ord-4bb030380e974bc88169e9b0d50458a6
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09353113B2

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