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Sodium hydride → methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate

HRID 322932
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Reaktionsgleichung

Reaktionsgleichung von HRID 322932
[C:1]([NH:9][CH:10](P(OC)(OC)=O)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23]([O:30][C:31]1[CH:38]=[C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:36]=[CH:35][C:32]=1[CH:33]=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:1]([NH:9]/[C:10](=[CH:33]/[C:32]1[CH:35]=[CH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][C:31]=1[O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:1]([NH:9]/[C:10](=[CH:33]\[C:32]1[CH:35]=[CH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][C:31]=1[O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 14104867Methyl 2-benzamido-2-(dimethoxyphosphoryl)acetate

Produkt 2

HCID 22010495methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylateHCID 70223822methyl (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A stirred solution of methyl benzoylamino(dimethoxyphosphoryl)acetate (4.25 g) in dry tetrahydrofuran (30 mL) is treated with sodium hydride (0.66 g, 60% dispersion in mineral oil) under nitrogen. After stirring for 15 minutes a solution of 2,4-dibenzyloxybenzaldehyde (4.74 g) in dry tetrahydrofuran (15 mL) is added dropwise. The reaction mixture is stirred at room temperature for 18 hours, evaporated and the residue partitioned between ethyl acetate (100 mL) and water (75 mL). The organic phase is washed with brine (50 mL), dried over magnesium sulphate and evaporated. The residual yellow oil is purified by flash chromatography on silica eluting with initially with dichloro-methane then with a mixture of dichloromethane and ethyl acetate (9:1 v/v). Fractions homogeneous in the required products are evaporated to give methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate (1 g) as a yellow foam, and methyl (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)-acrylate (1.6 g) as a yellow oil.

Aufarbeitung

  1. additionis added dropwise
  2. customevaporated
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (75 mL)
  4. washThe organic phase is washed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residual yellow oil is purified by flash chromatography on silica eluting with initially with dichloro-methane
  8. additionwith a mixture of dichloromethane and ethyl acetate (9:1 v/v)
  9. customFractions homogeneous in the required products are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-da2bc403b35c40529730b4aeab800d13
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06211234B1

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