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2-Bromo-1-(4-chlorophenyl)ethan-1-ol → trans-6-(2,4-Dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyran

HRID 905070
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 905070
[Br:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]=[CH:19][O:18]1>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:12][C:13]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][C@@H:17]1[O:18][C@@H:19]([O:11][CH:3]([C:4]2[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=2)[CH2:2][Br:1])[CH2:20][CH2:21][CH2:22]1
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Komponenten

6

Edukt 2

HCID 2368002-Bromo-1-(4-chlorophenyl)ethan-1-olHCID 130712842-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran

Produkt 1

HCID 53718043trans-6-(2,4-Dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyranAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysator
HCID 24813
Phosphorus oxychloride
Katalysator
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 259 mg of α-bromomethyl-4-chlorobenzyl alcohol and 311 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran in 6 ml of diethyl ether was added one drop of phosphorus oxytrichloride, and the mixture was stirred at room temperature for 1 day. After 3 drops of triethylamine had been added, the solvent was evaporated off under reduced pressure and the residue was purified by column chromatography through silica gel eluted with a 5:50:11 by volume mixture of benzene, hexane and ethyl acetate, to give 147 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyran melting at 86°-87° C., 165 mg of the isomer of greater polarity melting at 97°-98° C., and 80 mg of a mixture thereof.

Aufarbeitung

  1. customthe solvent was evaporated off under reduced pressure
  2. customthe residue was purified by column chromatography through silica gel
  3. washeluted with a 5:50:11 by volume mixture of benzene, hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cdf87a7c11d84c979c5af835a820cb6a
Quelldatensatz
uspto-grants-1983_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04421758

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