Triethylamine → Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

HRID 449970

Reaktionsgleichung

Reaktionsgleichung von HRID 449970
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[C:9](=[N+:37]=[N-:38])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 64717392Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate

Produkt 1

HCID 86659989Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate (1.30 g, 5.31 mmol), triethylamine (0.618 g, 6.11 mmol, 1.15 equiv), and 4-acetamidobenzenesulfonyl azide (1.40 g, 5.85 mmol, 1.1 equiv) were combined in acetonitrile (15 mL). After stirred at ambient temperature for 30 minutes, the mixture was concentrated in vacuo and the residue was treated with sodium hydroxide (25 mL, 2 M aqueous) and extracted with twice chloroform. The combined organic extracts were washed once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate), providing the titled compound.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was treated with sodium hydroxide (25 mL, 2 M aqueous)
  3. extractionextracted with twice chloroform
  4. washThe combined organic extracts were washed once with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0a192c536ecd4edeaba4bb7374379d0c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486946B2

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