1-Acetoxy-2-bromoethane → Pivalic acid 6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 2424211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2424211
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:14]=[CH:13][C:12]=2[CH2:11]1.[C:27]([O:30][CH2:31][CH2:32]Br)(=[O:29])[CH3:28].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:31]([O:30][C:27]([CH2:28][NH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:25])[CH3:24])[CH:14]=[CH:13][C:12]=2[CH2:11]1)=[O:29])[CH3:32]

Komponenten

6

Edukt 4

HCID 135641-Acetoxy-2-bromoethaneHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 66626486Pivalic acid 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Produkt 1

HCID 57933970Pivalic acid 6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl esterAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of pivalic acid 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (110 mg), bromoethyl acetate (400 mg), sodium acetate (200 mg) and ethanol (2 ml) was refluxed overnight. A saturated aqueous solution of sodium bicarbonate was added, and the solution was extracted with ethyl acetate. The solution was washed with brine, dried over magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (83 mg).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-74eae0acc5a34e01805f774b2a58755a
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960412B2

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