Ethyl bromoacetate → (1RS,3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 862357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862357
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][CH3:24])[CH:19]=2)[CH:14]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[CH2:13]1.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C)C=O>[C:36]([CH2:35][O:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][CH3:24])[CH:19]=2)[CH:14]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[CH2:13]1)([O:38][CH2:39][CH3:40])=[O:37]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 217130923-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

Produkt 1

HCID 21713104(1RS,3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of sodium hydride (5 mg, 0.21 mmol) in dimethylformamide (0.5 ml) was added (1RS, 3RS)-3-(2-hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (0.058 g, 0.14 mmol) at ice-bath temperature under argon. After stirring for 15 min, ethyl bromoacetate (50 μl, 0.2 mmol) was added and the solution stirred for 1 h at room temperature. The product was partitioned between ethyl acetate and 3M aq HCl. The organic extract was washed with water, sat. aq. NaHCO3 solution and finally brine. After drying (MgSO4 anhydrous) filtration and evaporation followed by chromatography gave (1RS, 3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (0.041 g). The product was dissolved in hot ethanol (10 ml) and 1M aq. NaOH added (1 ml). The mixture was refluxed for 1 h then cooled, acidified with 6M-aqueous HCl and extracted with ethyl acetate. After evaporation the residue was crystallized from ethyl acetate/hexane to give the title compound (0.035 g, 93%). m.p. 177°-178° C.

Aufarbeitung

  1. stirringthe solution stirred for 1 h at room temperature
  2. customThe product was partitioned between ethyl acetate and 3M aq HCl
  3. extractionThe organic extract
  4. washwas washed with water, sat. aq. NaHCO3 solution and finally brine
  5. customAfter drying
  6. filtration(MgSO4 anhydrous) filtration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ef6f91b674494b49ad64c76e336e5dcd
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716984

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