2,4-Dichlorobenzyl alcohol → trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905055

Reaktionsgleichung

Reaktionsgleichung von HRID 905055
[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]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][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

6

Edukt 2

HCID 156842,4-Dichlorobenzyl alcoholHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 13073916trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyranAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysatorHCID 24813Phosphorus oxychlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran in 25 ml of diethyl ether were added 1.06 g of 2,4-dichlorobenzyl alcohol, followed by a catalytic amount (2-3 drops) of phosphorus oxytrichloride. The mixture was then stirred at room temperature for 4 days, after which 3 drops of triethylamine were added to the mixture, which was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel as in Example 1(a), to give 1.82 g of trans-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the lesser polarity), 144 mg of cis-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the greater polarity) and 200 mg of a cis/trans mixture.

Aufarbeitung

  1. concentrationwas then concentrated by evaporation under reduced pressure
  2. customThe residue was purified by column chromatography through silica gel as in Example 1(a)

Quellen und Nachweise

ORD-Eintrag
ord-963b87fab3af4ff0bf5eb899ec0cab23
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421758

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