Hexane → methyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

HRID 1713933

Reaktionsgleichung

Reaktionsgleichung von HRID 1713933
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][Si](C=[N+]=[N-])(C)C.CCCCCC.[N+](=C)=[N-]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:16])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 9550DiazomethaneHCID 167693TrimethylsilyldiazomethaneHCID 6149193-(4-Chloro-3-nitrophenyl)acrylic acid

Produkt 1

HCID 28818827methyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-3-nitrocinnamic acid in a mixture of methanol/DCM (1:1, v/v, 0.09 M), a 2 M solution of trimethylsilyl diazomethane in hexane (4 eq) was slowly added until the yellow color persisted, indicating an excess of diazomethane. The resulting mixture was evaporated. PE was added to the residue and the resultant precipitate was filtered and dried under vacuo to afford the title compound (97%) as a solid. 1H NMR (400 MHz; DMSO-d6, 300 K) δ 3.75 (s, 3H), 6.86 (d, J 16, 1H), 7.73 (d, J 16, 1H), 7.84 (d, J 8.4, 1H), 8.08 (d, J 8.4, 1H), 8.48 (s, 1H); MS (ES+) m/z 242 (M+H)+.

Aufarbeitung

  1. customThe resulting mixture was evaporated
  2. additionPE was added to the residue
  3. filtrationthe resultant precipitate was filtered
  4. customdried under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9b3887cbe5a844a3b63d906cc37a2fe8
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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