Water → HCID 19976898, Verbindung

HRID 1450641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1450641
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9]Cl)=O)=[CH:5][CH:4]=1.[CH:13]#[C:14][CH:15]([OH:18])[CH2:16][CH3:17].C(N(CC)CC)C.[OH2:26]>C1C=CC=CC=1>[OH:18][CH:15]([C:16]1[O:26][N:9]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=1)[CH2:14][CH3:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 929811-Pentyn-3-olHCID 21579386N-Chloro-4-methoxybenzamide

Produkt 1

HCID 19976898HCID 19976898, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To a solution of 79.8 g (43 mmol) of 4-methoxybenzhydroxamic acid chloride and 7.23 g (86 mmol) of 1-pentyn-3-ol in 160 ml of benzene, a solution of 6.53 g (64.5 mmol) of triethylamine in 80 ml of benzene was added dropwise while maintaining the internal temperature at 3°-5° C. After the mixture was stirred for 2 hours, water was added so that the reaction product was extracted in the organic layer. The organic layer was separated and collected and the solvent was distilled off, whereby an oily residue was obtained. The oily residue was purified by silica gel chromatography (eluent: 30:1 chloroform/methyl alcohol), so that the title compound was obtained as yellow oil [yield: 8.07 g (81%)].

Aufarbeitung

  1. temperaturewhile maintaining the internal temperature at 3°-5° C
  2. extractionwas extracted in the organic layer
  3. customThe organic layer was separated
  4. customcollected
  5. distillationthe solvent was distilled off
  6. customwhereby an oily residue was obtained
  7. customThe oily residue was purified by silica gel chromatography (eluent: 30:1 chloroform/methyl alcohol), so that the title compound
  8. customwas obtained as yellow oil [yield: 8.07 g (81%)]

Quellen und Nachweise

ORD-Eintrag
ord-851347d028ff47a1b3d7f54c890645d2
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602160

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