Hydrochloric Acid → 1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 650758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650758
O[C:2]1([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]1[C:17]([O:19]CC)=[O:18].C([SiH](CC)CC)C.B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH2:29]1[O:28][C:25]2[CH:26]=[CH:27][C:22]([CH:2]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:3]3[C:17]([OH:19])=[O:18])=[CH:23][C:24]=2[O:30]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18969644Ethyl(1RS)-1-Hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate

Produkt 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acidAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl (1RS)-1-hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate (1.03 g, 2.58 mmol) in CH2Cl2 (40 mL) was added triethylsilane (0.49 ml, 3.07 mmol), followed by boron trifluoride etherate (1.55 ml, 12.6 mmol). The reaction mixture was allowed to stir for 15 min, at which time was added slowly 3M HCl. The mixture was extracted with EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (1.00 g, 100%) as a mixture of Δ1 and Δ2 double bond isomers.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl
  4. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e63b8627823a4eb8a9ed929d413af90d
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274737B1

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