Acetic Acid → HCID 54432946, Verbindung

HRID 483991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483991
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([O:12][P:13]([CH2:22][CH2:23][CH2:24][NH2:25])([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[O:14])[CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:10]([O:12][P:13]([CH2:22][CH2:23][CH2:24][NH:25][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[O:14])[CH3:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Produkt 1

HCID 54432946HCID 54432946, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

1.41 g of p-chlorobenzaldehyde are added to a solution of 2.53 g of 3-aminopropyl(diethoxymethyl)phosphinic acid ethyl ester in 10 ml of anhydrous methanol, and the resulting clear solution is stirred at room temperature for 30 minutes. There are then added first 0.6 g of glacial acetic acid and then, dropwise, 0.21 g of sodium cyanoborohydride in solution in 5 ml of methanol. An exothermic reaction begins. The mixture is stirred at 20° for 3 hours and adjusted to pH 8, and the solvent is removed. The residue is dissolved in dichloromethane and washed with water. The organic phase is separated off, dried over sodium sulfate and concentrated to dryness by evaporation. The oil that remains is purified by chromatography on silica gel, yielding 3-(p-chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester in the form of a yellowish oil.

Aufarbeitung

  1. customAn exothermic reaction
  2. stirringThe mixture is stirred at 20° for 3 hours
  3. customthe solvent is removed
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washwashed with water
  6. customThe organic phase is separated off
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness by evaporation
  9. customThe oil that remains is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0a7d03df098d4b8fbfac141aa4c9c907
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229379

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