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CID 406 → Methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

HRID 257626
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 257626
[Na].[C:2]1([C:8]2[N:9]=[C:10]([CH2:19]P(=O)(OC)OC)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([C:28]1[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=1)[O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=O.P(=O)([O-])[O-]>CO>[C:2]1([C:8]2[N:9]=[C:10]([CH:19]=[CH:26][C:28]3[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=3)[O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[O:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

6

Edukt 4

HCID 406CID 406HCID 1494380Methyl 2-(3-formylphenoxy)acetateHCID 5360545SodiumHCID 54445617Dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate

Produkt 1

HCID 53907733Methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

Sodium metal (260 mg, 11 mg atom) was dissolved in methanol (50 mL) and dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate (3.89 g, 11 mmol) added followed by methyl (3-formylphenoxy)acetate (2 g, 10 mmol). The mixture was stirred at room temperature for 20 minutes before being concentrated and diluted with 2N HCl solution. The mixture was extracted with CH2Cl2, the organic phase dried over sodium sulfate and the solvent evaported to leave a yellow oil. This was combined with the crude material from a reaction performed on 2 g of the phosphonate and 985 mg of aldehyde and chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (3:2) furnished methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate as the diethyl ether solvate (2.92 g, 46%) after recrystallization from diethyl ether, m.p. 79°-82° C.

Aufarbeitung

  1. concentrationbefore being concentrated
  2. additiondiluted with 2N HCl solution
  3. extractionThe mixture was extracted with CH2Cl2
  4. dry with materialthe organic phase dried over sodium sulfate
  5. customto leave a yellow oil
  6. customchromatographed on a column of silica gel
  7. washElution
  8. additionwith a mixture of hexanes and diethyl ether (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-b6b259a1f7cc441f9591b6800a523a2e
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05262540

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