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

HRID 1269595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269595
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12]C)=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20].[BH4-].[Na+]>CO>[CH2:17]([NH:21][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[CH2:18][CH2:19][CH3:20]

Komponenten

5

Edukt 3

HCID 8007ButylamineHCID 4311764Sodium borohydrideHCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetate

Produkt 1

HCID 58622898Methyl {4-[(butylamino)methyl]-2-methylphenoxy}acetateAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (0.65 g, 2.93 mmol) in anyhdrous methanol (12 mL) under nitrogen was added n-butylamine (0.3 mL, 3.07 mmol) and the resultant mixture stirred for 18 h at room temperature, prior to portion wise addition of sodium borohydride (0.144 g, 3.8 mmol). After 30 minutes stirring at room temperature the reaction was quenched by cautious addition of sat. sodium bicarbonate aq. and then extracted into ethyl acetate (2×40 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a pale yellow oil (0.65 g).

Aufarbeitung

  1. customwas quenched by cautious addition of sat. sodium bicarbonate aq.
  2. extractionextracted into ethyl acetate (2×40 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-090f2d890ff540a680fbf234dbedced4
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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