Water → 5-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol

HRID 1772

Reaktionsgleichung

Reaktionsgleichung von HRID 1772
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH:22]=O.[BH4-].[Na+].O>C(O)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[O:19][CH3:18])=[C:3]([CH:13]=1)[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 11437092(2-Amino-5-chlorophenyl)(2-chlorophenyl)methanol

Produkt 1

HCID 538414955-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcoholAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product.

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  3. washThe ethyl acetate layer was washed with 1N sodium hydroxide, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-8208d819f879448fbecf7d2aa5f1ad04
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726306

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