Hydrochloric Acid → 4-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

HRID 24932

Reaktionsgleichung

Reaktionsgleichung von HRID 24932
N1C=CC=CC=1.[OH:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>ClCCl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:7][CH2:8][C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 50337133-(4-Nitrophenyl)prop-2-yn-1-ol

Produkt 1

HCID 225692544-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4.4 ml (54 mmol) of pyridine are added dropwise to a solution of 5.8 g (33 mmol) of 4-(3-hydroxyprop-1-ynyl)-nitrobenzene and 5.2 g (27 mmol) of p-toluenesulphonic acid chloride in 50 ml of dichloromethane at 0° C. After 2 hours at 0° C. about 25 g of ice and 8 ml of conc. hydrochloric acid are added. The organic phase is separated off and washed with water. After removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product is obtained as an oil.

Aufarbeitung

  1. customThe organic phase is separated off
  2. washwashed with water
  3. customAfter removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product
  4. customis obtained as an oil

Quellen und Nachweise

ORD-Eintrag
ord-609c1b4a63564df49883e9626a456c92
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855710B2

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