Acetic Acid → Ethyl 2-[3-[N-(4-Chlorobenzyl)aminomethyl]phenoxy]-2-methylpropionate

HRID 480684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480684
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][CH2:1][C:3]2[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=2)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 660364-ChlorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoate

Produkt 1

HCID 18766446Ethyl 2-[3-[N-(4-Chlorobenzyl)aminomethyl]phenoxy]-2-methylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Ethyl 2-(3-formylphenoxy)-2-methylpropionate (25 g, 105.8 mmol) was dissolved in 1,2-dichloroethane (300 mL). Subsequently, 4-chlorobenzylamine (15.44 mL, 127.0 mmol) and acetic acid (7.26 mL, 127.0 mmol) were added thereto, and the resultant mixture was stirred for 20 minutes at 0° C. Subsequently, sodium (triacetoxy)borohydride [NaBH(OAc)3 (26.91 g, 127.0 mmol)] was added thereto, and the mixture was stirred for five hours at room temperature. After completion of reaction, chloroform was added. Washing was performed sequentially with aqueous saturated sodium bicarbonate, water, and saturated brine, followed by drying over magnesium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil was obtained (35.27 g, 92%).

Aufarbeitung

  1. additionwas added
  2. washWashing
  3. dry with materialby drying over magnesium sulfate
  4. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil
  5. customwas obtained (35.27 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-391fd4c2304d4c708005fedc0f65078d
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653334B1

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