Acetic Anhydride → 3-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

HRID 986698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986698
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18])=[CH:15][C:14]=2[Br:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[O:18])=[CH:15][C:14]=2[Br:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[O:34][C:35](=[O:37])[CH3:36])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 137681403-(N,N-dimethylamino)propyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate

Produkt 1

HCID 137456293-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In a mixture of pyridine (5 ml) and acetic anhydride (5 ml) was dissolved 3-(N,N-dimethylamino)propyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate (1 g). The solution was stirred at 110° to 120° C. for about 18 hours, followed by concentration. The residue was chromatographed on a column of silica gel. The elution was conducted with ethyl acetate, and the eluate was evaporated. The resulting oily substance was dissolved in ether, to which was added an ether solution of anhydrous oxalic acid. The resultant crystals were collected by filtration, which were washed with ethanol and then with isopropyl ether, followed by drying to give 866 mg of 3-(N,N-dimethyl-amino)propyl 4-[3-(4-acetyl-3-acetoxy-2-propylphenoxy)propoxy]-3-bromobenzoate.mono-oxalate, m.p. 141°-142° C.

Aufarbeitung

  1. concentrationfollowed by concentration
  2. customThe residue was chromatographed on a column of silica gel
  3. washThe elution
  4. customthe eluate was evaporated
  5. dissolutionThe resulting oily substance was dissolved in ether, to which
  6. additionwas added an ether solution of anhydrous oxalic acid
  7. filtrationThe resultant crystals were collected by filtration, which
  8. washwere washed with ethanol
  9. customby drying

Quellen und Nachweise

ORD-Eintrag
ord-0326efcbcf7d4fffb6e9e75556b33592
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04714774

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