Cyclopropylacetylene → HCID 86702007, Verbindung

HRID 717979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717979
Cl[C:2]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)=[O:3].[C:13]([CH:15]1[CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.CO.[Cu]I>[CH:15]1([C:13]#[C:14][C:2]([C:4]2[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=2)=[O:3])[CH2:17][CH2:16]1

Komponenten

6

Edukt 2

HCID 138823CyclopropylacetyleneHCID 21779986Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate

Produkt 1

HCID 86702007HCID 86702007, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate (500 mg, 2.443 mmol) was dissolved in triethylamine (5 mL) and the suspension was degassed with nitrogen. Copper(I) iodide (40 mg, 0.210 mmol) and bistriphenylphosphine palladium (II) chloride (40 mg, 0.057 mmol) were added followed by ethynylcyclopropane (162 mg, 2.443 mmol). The mixture was stirred overnight, diluted with methanol and concentrated to dryness. The crude material was partitioned between dichloromethane and water. The organic extracts were dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.

Aufarbeitung

  1. customthe suspension was degassed with nitrogen
  2. concentrationconcentrated to dryness
  3. customThe crude material was partitioned between dichloromethane and water
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cbf5339cbc8242349c835f8003b0290c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193723B2

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