Hydrochloric Acid → Benzyl-N,N-dimethylglycolamide

HRID 2293495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293495
[Cl-].[CH3:2][N:3]([Al+]C)[CH3:4].[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]([CH3:4])[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 dimethylamino(methyl)aluminum chloride [prepared from dimethylamine hydrochloride (3.4 g, 42 mmol) and trimethyl aluminum (21 ml, of 2M 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 3N 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): δ7.4-7.1 (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-c5bf19594412486cbfbf19f8bddad4dd
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686455

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