Acetic Acid → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)acrylamide

HRID 735171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735171
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][C:21]([CH2:24][OH:25])=[CH:22][CH:23]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 86601892(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide

Produkt 1

HCID 68819611(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4.4 g (12.16 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide in 200 mL of THF is adjusted with glacial acetic acid to a pH of three, combined with 8.14 g (36.48 mmol) of sodium triacetoxyborohydride, and stirred for 18 hours at ambient temperature. Then the reaction mixture is poured into water and the precipitate is filtered off. The filtrate is extracted with ethyl acetate, washed with water, and dried over sodium sulfate. The solvent is removed and the residue is combined with the solid which has been filtered off. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (30:1:0.1)). Yield: 3.2 g (72.4% of theory); C22H18ClNO2 (M=363.84); calc.: molecular ion peak (M+H)+: 364/366; found: molecular ion peak (M+H)+: 364/366; Rf value: 0.2 (silica gel, dichloromethane/ethanol (20:1)).

Aufarbeitung

  1. filtrationthe precipitate is filtered off
  2. extractionThe filtrate is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed
  6. filtrationhas been filtered off
  7. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-da7c9d8be14042e593bb3fd5d9ae238a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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