(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate → Trans-6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran

HRID 905062

Reaktionsgleichung

Reaktionsgleichung von HRID 905062
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[CH:4][CH:3]=1.[S:18]([O:28][CH2:29][CH:30]1[CH2:35][CH2:34][CH:33]=[CH:32][O:31]1)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:17][C@@H:32]2[O:31][C@@H:30]([CH2:29][O:28][S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=3)(=[O:19])=[O:20])[CH2:35][CH2:34][CH2:33]2)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonateHCID 225654352,4,4'-Trichlorobenzhydrol

Produkt 1

HCID 53867744Trans-6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 24813Phosphorus oxychlorideKatalysator

Versuchsvorschrift

2.10 g of α-(4-chlorophenyl)-2,4-dichlorobenzyl alcohol and 1.78 of 2-tosyloxymethyl-3,4-dihydro-2H-pyran were dissolved in 40 ml of diethyl ester, and a catalytic amount (2 drops) of phosphorus oxytrichloride was added to the solution. The mixture was then stirred at room temperature for 4 days, after which 3 drops of triethylamine were added. The mixture was then concentrated by evaporation under reduced pressure and the residue was purified by column chromatography through silica gel eluted with a 15:5:1 by volume mixture of hexane, benzene and ethyl acetate, to give 3.41 g of the title compound in the form of a colourless oil.

Aufarbeitung

  1. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography through silica gel
  3. washeluted with a 15:5:1 by volume mixture of hexane, benzene and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b6aa40c21ef24b06a2d1e5d660883ff9
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421758

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