Butylamine → Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

HRID 1269590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269590
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[CH2:17]([NH:21][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[CH2:18][CH2:19][CH3:20]

Komponenten

5

Edukt 3

HCID 8007ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetate

Produkt 1

HCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetateAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (3 g, 13.5 mmol) in anhydrous ethanol (50 mL) at room temperature, was added n-butylamine (1.6 mL, 16.2 mmol) and 4A molecular sieves. The resultant mixture was stirred at room temperature for 18 h under nitrogen, prior to portion wise addition of sodium triacetoxyborohydride (3.43 g, 16.2 mmol). After a further 3 h stirring at room temperature, the reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL) and then diluted with water (50 mL), before extracting with EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as brown oil (2.6 g).

Aufarbeitung

  1. customthe reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL)
  2. additiondiluted with water (50 mL)
  3. extractionbefore extracting with EtOAc (2×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b84e7ef73b164e4cb7221d2f1da49fde
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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