Sodium Chloride → 1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene

HRID 704907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704907
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[F:15])[CH2:10][OH:11])=[CH:4][CH:3]=1.[H-].[Na+].[F:20][C:21]([F:35])([F:34])[C:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)=[CH:23]Cl.[Cl-].[Na+]>CN(C)C=O.O>[F:20][C:21]([F:34])([F:35])[C:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)=[CH:23][O:11][CH2:10][C:9]1[CH:12]=[CH:13][C:14]([F:15])=[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 159177183-(4-Chlorophenoxy)-4-fluorobenzyl alcoholHCID 540539251,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene

Produkt 1

HCID 537269141,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-eneAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of 3-(4-chlorophenoxy)-4-fluorobenzyl alcohol (6.3 g) in N,N-dimethylformamide (20 cm3) was added to a stirred suspension of sodium hydride (1.2 g of a 50% dispersion in oil) in N,N-dimethylformamide. After 30 minutes, this mixture was added to a stirred solution of EZ-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene (5 g) in N,N-dimethylformamide (25 cm3) at a temperature maintained at -10° C. during the addition. After 45 minutes the reaction mixture was poured into water (150cm3) and sodium chloride added. The products were extracted into diethyl ether (4×100 cm3), and the combined organic layers were dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure. The crude residue was purified by column chromatography on a silica gel support, eluted with n-hexane containing 6% by volume diethyl ether, to give 1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene (6 g).

Aufarbeitung

  1. additionadded
  2. extractionThe products were extracted into diethyl ether (4×100 cm3)
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulphate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe crude residue was purified by column chromatography on a silica gel support
  6. washeluted with n-hexane containing 6% by volume diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f29bb38096944f6aa66249551165d3d9
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988826

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