Hydrochloric Acid → Benzyl-N,N-dimethylglycolamide

HRID 1387625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387625
[Cl-].[CH3:2][N:3]([CH3:6])[Al+]C.[CH2:7]([CH:14]([OH:19])[C:15](OC)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1(C)C=CC=CC=1>[CH2:7]([CH:14]([OH:19])[C:15]([N:3]([CH3:6])[CH3:2])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 518800Methyl 2-hydroxy-3-phenylpropanoateHCID 86751577Dimethylamino(methyl)aluminum chloride

Produkt 1

HCID 18771503Benzyl-N,N-dimethylglycolamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To dimethyl-amino(methyl)aluminum chloride [prepared from dimethylamine hydrochloride (3.4 g, 42 mmoL) and trimethyl aluminum (21 mL of 2 M solution, 42 mmol)] in toluene (40 mL) was added methyl benzylglycolate (3.0 g, 17 mmol). After stirring at rt for 1.5 h, the mixture was poured into 3 N HCl and extracted with Et2O. The organic extract was washed with saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 9-50% EtOAc/Hex. The title compound was obtained as a colorless oil (1.2 g, 37%): 1H NMR (CDCl3): d 7.4-7.1 (m, 5H); 4.61 (s, 2H); 4.18 (s, 2H); 2.98 (s, 3H); 2.95 (s, 3H).

Aufarbeitung

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with a solvent gradient of 9-50% EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-119f9965cb21464aa2bbc91be8919e44
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268370B1

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