Formaldehyde → 4-[Ethyl-[(4-methoxyphenyl)methyl]amino]but-2-yn-1-ol

HRID 1489219

Reaktionsgleichung

Reaktionsgleichung von HRID 1489219
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[CH2:13]=O.[CH2:15]([OH:18])[C:16]#[CH:17].CO>O1CCOCC1.C(Cl)Cl.Cl[Cu]>[CH2:1]([N:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[CH2:13][C:17]#[C:16][CH2:15][OH:18])[CH3:2]

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 887MethanolHCID 7859Propargyl alcoholHCID 296018Benzenemethanamine, N-ethyl-4-methoxy-

Produkt 1

HCID 42481904-[Ethyl-[(4-methoxyphenyl)methyl]amino]but-2-yn-1-olAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of N-ethyl-4-methoxybenzenemethanamine (13.3 g, 80.6 mmol), paraformaldehyde (3.63 g), propargyl alcohol (6.33 g, 113 mmol) and CuCl (0.311 g) in 350 mL of 1,4-dioxane was stirred at reflux for 30 min. The reaction mixture was cooled to room temperature and concentrated. The residue was diluted with 200 mL of 50% NH4OH and extracted with EtOAc. The combined extracts were washed with water, brine, dried and concentrated. The residue was chromatographed on silica gel (elution with 2.5% MeOH in CH2Cl2 and then 5% MeOH in CH2Cl2) to afford the product V (15.1 g, 81% yield) as an oil.

Aufarbeitung

  1. temperatureat reflux for 30 min
  2. concentrationconcentrated
  3. additionThe residue was diluted with 200 mL of 50% NH4OH
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel (
  9. washelution with 2.5% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4198ee4fc3ac45658c164ca884ce11be
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677346

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