Methanol → HCID 86675044, Verbindung

HRID 1912075

Reaktionsgleichung

Reaktionsgleichung von HRID 1912075
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:21](=O)[C:22]#[C:23][CH:24]1[CH2:27][CH:26]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25]1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl-].[CH3:44][O:45][NH3+:46]>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:21](=[N:46][O:45][CH3:44])[C:22]#[C:23][CH:24]1[CH2:27][CH:26]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25]1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11639O-methylhydroxylammonium chlorideHCID 24436Sodium SulfateHCID 71127328tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-oxo-5-hexynoate

Produkt 1

HCID 86675044HCID 86675044, VerbindungAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-oxo-5-hexynoate (3.44 g) and methanol (35 mL) were mixed. To the mixture were added sodium sulfate (2.15 g), pyridine (3.5 mL) and O-methylhydroxylammonium chloride (1.26 g). The mixture was stirred at RT overnight. The mixture was then filtered, and the filtrate was concentrated in vacuo. To the resultant residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. To the resultant residue was added silica gel (5 g), and the mixture was stirred at RT for 10 min. The silica gel was filtered off and the filtrate was concentrated in vacuo to give the title compound (3.38 g) as a crude product.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the resultant residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. concentrationthe filtrate was concentrated in vacuo
  9. additionTo the resultant residue was added silica gel (5 g)
  10. stirringthe mixture was stirred at RT for 10 min
  11. filtrationThe silica gel was filtered off
  12. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8c793229826f4136a906034c99bc1f03
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604069B2

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