2-Bromoanisole → 1-(2-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650405
O[C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)=[C:3]1[C:20]([O:22]CC)=[O:21].[Mg].BrC1C=CC=CC=1OC.COC1C=CC=CC=1[Mg]Br.C1OC2C=CC(C3C4C(=CC=CC=4)C(=O)C=3C(OCC)=O)=CC=2O1>C1COCC1.C1COCC1.CCOCC>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)[CH:3]1[C:20]([OH:22])=[O:21]

Komponenten

8

Edukt 5

HCID 113582-BromoanisoleHCID 5462224MagnesiumHCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylateHCID 18969641Ethyl (1RS) 1-Hydroxy-1-(methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indene-2-carboxylateHCID 178489560HCID 178489560, Verbindung

Produkt 1

HCID 187039001-(2-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21868444Ether tetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl (1RS)-1-Hydroxy-1-(2-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate. To dry magnesium turnings (81 mg, 3,4 mmol) under an argon atmosphere was added a solution of 2-bromoanisole (0.64 g, 3.4 mmol) in 5:1 THF/Et2O (3 ml). A portion of the resulting 2-methoxyphenyl magnesium bromide solution (0.45 ml, 0.51 mmol) was added dropwise to a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (100 mg, 0.34 mmol) in THF (6 ml) under an argon atmosphere at 0° C. After stirring for 15 min, the mixture was partitioned between 3M HCl and EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 15% EtOAc/hexanes to afford the title compound. (100 mg, 68%).

Aufarbeitung

  1. customthe mixture was partitioned between 3M HCl and EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluting with 15% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3c72d7f638d84ce8a77650922b6c27de
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271399B1

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