Acetic Acid → Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

HRID 362284

Reaktionsgleichung

Reaktionsgleichung von HRID 362284
[H-].[Na+].[C:3]([O:12]C)(=[O:11])[CH2:4][O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH3:24].C(O)(=O)C>C1C=CC=CC=1.O>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[C:6](\[O:5][CH2:4][C:3]([OH:12])=[O:11])/[C:7]([O:9][CH3:10])=[O:8])=[CH:30][CH:29]=1)[CH3:24]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2018771,1'-Dimethyl 2,2'-oxybis(acetate)HCID 100402134-[2-(N-Methyl-N-(2-benzoxazolyl)amino)ethoxy]benzaldehyde

Produkt 1

HCID 86753267Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of sodium hydride (60% dispersion in mineral oil. 0.30 g), dimethyl diglycolate (0.81 g) and 4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]benzaldehyde (2.22 g) in dry benzene (50 mL) was stirred at room temperature overnight. Acetic acid (1 mL) was added, the mixture was poured onto iced water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with water, dried (MgSO4) and evaporated. The resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane, and the product crystallised from ethyl acetate, mp 111°-112° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane
  6. customthe product crystallised from ethyl acetate, mp 111°-112° C.

Quellen und Nachweise

ORD-Eintrag
ord-349088323bb042b2b50b80f050556ffa
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869495

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