Hydrochloric Acid → 1-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

HRID 217731

Reaktionsgleichung

Reaktionsgleichung von HRID 217731
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)[C:8](N(OC)C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Mg]Br.Cl>C1COCC1.O>[C:1]([C:5]1[CH:6]=[C:7]([C:8](=[O:9])[CH3:22])[CH:14]=[C:15]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 581368013-tert-butyl-N-methoxy-5-(2-methoxyethoxy)-N-methylbenzamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 581368081-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-tert-Butyl-N-methoxy-5-(2-methoxyethoxy)-N-methylbenzamide (O3.043; 1.35 g) was dissolved in THF (40 ml), methylmagnesium bromide (3.05 ml, 3 M in ether) was added dropwise at 0° C. and then the mixture was stirred at RT for 2 h. Then the mixture was admixed with 1 N hydrochloric acid (50 ml), diluted with water and extracted by shaking three times with EA. Then the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min). 1.0 g of the title compound were obtained.

Aufarbeitung

  1. extractionextracted
  2. stirringby shaking three times with EA
  3. dry with materialThen the combined EA phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min)

Quellen und Nachweise

ORD-Eintrag
ord-2523aad047a645b588a41639490305d2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198272B2

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