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4-Toluenesulfonyl chloride → 5-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene

HRID 1271267
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1271267
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]2O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chloride2×HCID 229319625-(Benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 229320125-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthaleneAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 5.96 g of 5-(benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene in 23 ml of anhydrous pyridine, 4.37 g of p-toluenesulfonyl chloride was added. After stirring with heating at 70° C. for 3 hours, 0.72 g of p-toluenesulfonyl chloride was further added, followed by stirring for 1.5 hours. The reaction solution was extracted with diethyl ether after adding iced water. The extract was washed in turn with water, 10% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.79 g of the desired compound as a colorless crystal having a melting point of 64 to 67° C.

Aufarbeitung

  1. stirringby stirring for 1.5 hours
  2. extractionThe reaction solution was extracted with diethyl ether
  3. additionafter adding iced water
  4. washThe extract was washed in turn with water, 10% hydrochloric acid, water
  5. dry with materialan aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-493c496a3d754fec87ce91a7b5292abd
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07205302B2

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