Triethylamine → Methyl 4-(chloromethyl)cinnamate

HRID 618763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618763
O[CH2:2][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.CS([Cl:26])(=O)=O>C(Cl)Cl>[Cl:26][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54313853Methyl 4-(hydroxymethyl)cinnamate

Produkt 1

HCID 53426371Methyl 4-(chloromethyl)cinnamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of methyl 4-(hydroxymethyl)cinnamate (4.1 g), triethylamine (3.1 ml) and methylene chloride (50 ml) was added dropwise under ice cooling methanesulfonyl chloride (1.7 ml), and the mixture was stirred at room temperature for 1.5 hours. Evaporation of the reaction solution gave a residue, which was then chromatographed on silica gel column (eluent: methylene chloride) to give methyl 4-(chloromethyl)cinnamate (2.57 g).

Aufarbeitung

  1. additionwas added dropwise under ice
  2. customEvaporation of the reaction solution
  3. customgave a residue, which
  4. customwas then chromatographed on silica gel column (eluent: methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-f3a3de5552354205a5016cd709b7de46
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05955505

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