Benzenemethanol, 2,6-dichloro- → trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905058

Reaktionsgleichung

Reaktionsgleichung von HRID 905058
[S:1]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][O:23][C@@H:15]1[O:14][C@@H:13]([CH2:12][O:11][S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])[CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 2

HCID 27156Benzenemethanol, 2,6-dichloro-HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 54030357trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyranAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24813Phosphorus oxychlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran and 1.06 g of 2,6-dichlorobenzyl alcohol in 25 ml of diethyl ether was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and then the mixture was stirred at room temperature for 4 days. The colourless crystals which had precipitated were filtered off, giving 1.582 g of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, melting at 123°-124° C. Triethylamine was then added to the mother liquor and the resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography through silica gel, in essentially the same manner as described in Example 1(a), to give 338 mg of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran and 306 mg of cis-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran.

Aufarbeitung

  1. customThe colourless crystals which had precipitated
  2. filtrationwere filtered off

Quellen und Nachweise

ORD-Eintrag
ord-89332c3cc6314095a42f066bc7580a28
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421758

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