Water → 5-(Benzyloxy)-2-(chloromethyl)-3,4-dihydronaphthalene
Reaktionsgleichung
[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]([CH2:19]O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([Cl:30])(=O)=O)=CC=1.C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[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]([CH2:19][Cl:30])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Under an argon atmosphere, to a solution of 1.82 g of 5-(benzyloxy)-2-(hydroxymethyl)-3,4-dihydronaphthalene and 0.55 g of 4-(dimethylamino)pyridine in 30 ml of dichloromethane, 1.43 g of p-toluenesulfonyl chloride was added. After 1.2 ml of triethylamine was added dropwise, the mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into iced water and then extracted with diethyl ether. The extract was washed in turn with 5% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.06 g of the desired compound as a colorless oily substance.
Aufarbeitung
- extractionextracted with diethyl ether
- washThe extract was washed in turn with 5% hydrochloric acid, water
- dry with materialan aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-86fa57b7215a4f6eb1838bf422b7b0c7
- Quelldatensatz
- uspto-grants-2007_04
- Patentnummer
- US07205302B2
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