4-Chlorobenzyl alcohol → trans-6-(4-Chlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905053

Reaktionsgleichung

Reaktionsgleichung von HRID 905053
[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][C:23]([CH2:24][OH:25])=[CH:22][CH:21]=1>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:25][C@@H:15]2[O:14][C@@H:13]([CH2:12][O:11][S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:3])=[O:2])[CH2:18][CH2:17][CH2:16]2)=[CH:22][CH:21]=1

Komponenten

6

Edukt 2

HCID 133974-Chlorobenzyl alcoholHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 13261931trans-6-(4-Chlorobenzyloxy)-2-tosyloxymethyltetrahydropyranAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysatorHCID 24813Phosphorus oxychlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

3 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran and 1.91 g of p-chlorobenzyl alcohol were dissolved in 40 ml of diethyl ether, and 2-3 drops of phosphorus oxytrichloride were added to the resulting solution. The mixture was then allowed to react at room temperature for 1.5 days, after which 2 drops of triethylamine were added and the mixture was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, eluted with a 8:1 by volume mixture of hexane and ethyl acetate, to give 3.44 g of trans-6-(4-chlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the lesser polarity), 0.59 g of cis-6-(4-chlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the greater polarity) and 0.86 g of an approximately 1:1 cis/trans mixture.

Aufarbeitung

  1. customto react at room temperature for 1.5 days
  2. concentrationthe mixture was concentrated by evaporation under reduced pressure
  3. washeluted with a 8:1 by volume mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-10a4d67faeae4178a03af7919c790598
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421758

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