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

HRID 650750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650750
O[C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[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].C([SiH](CC)CC)C.B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]([C:11]3[CH:16]=[CH:15][C:14]4[O:17][CH2:18][O:19][C:13]=4[CH:12]=3)[CH:3]2[C:20]([OH:22])=[O:21])[CH:30]=[CH:29][CH:28]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18969638Ethyl(1RS)-1-Hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxypheny)indene-2-carboxylate

Produkt 1

HCID 159085021-(3-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl (1RS)-1-hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)-indene-2-carboxylate (150 mg, 0.35 rmnol) in CH2Cl2 was added triethylsilane (67 μl, 0.42 mmol), followed by boron trifluoride etherate (213 μl, 1.73 mmol). The reaction mixture was allowed to stir for 30 min, at which time was added slowly 5% aqueous HCl. The mixture was extracted with EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes to provide the title compound (45 mg, 31%) 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, H2O and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography
  7. washeluting with 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-89ac364444d94bcebcf8e81536e57a04
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274737B1

Notizen zur Reaktion

Wird geladen…