2-Methylaziridine → E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester

HRID 583542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583542
C[CH2:2][N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].BrC/C=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].CC1CN1>C1COCC1.CCOC(C)=O>[CH2:15]([O:14][C:12](=[O:13])/[CH:11]=[CH:7]/[CH2:6][N:3]1[CH2:2][CH:4]1[CH3:5])[CH3:16]

Komponenten

6

Edukt 3

HCID 63772-MethylaziridineHCID 8471TriethylamineHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Produkt 1

HCID 88285506E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add 10 mL of NEt3 to a solution of 9.2 mL of ethyl 4-bromocrotonate and 4 mL of 2-methylaziridine in 100 mL of THF. Stir for 60 h, during which time a white precipitate forms. Dilute the reaction mixture with 300 mL of EtOAc and wash with water and then with brine. Dry the organic solution over MgSO4, filter, and concentrate in vacuo to yield 6.7 g of crude product. Purify by flash chromatography (silica gel, 1:4 hexane/EtOAc) to yield 5.2 g of E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester.

Aufarbeitung

  1. washwash with water
  2. dry with materialDry the organic solution over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto yield 6.7 g of crude product
  6. customPurify by flash chromatography (silica gel, 1:4 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e6cae2f647df41f1a90721635c5d5780
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929236

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