Isopropanol → 3-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid

HRID 650421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650421
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2C(O)=O)=[C:5]([O:34][CH2:35]OC)[CH:4]=1.COC1C=CC(C2C3C(=CC=C(OCCC)C=3)C(C3C=CC4OCOC=4C=3)[CH:47]2[C:68]([O-:70])=[O:69])=C(OCOC)C=1.[OH-:75].[Na+].[CH:77]([OH:80])(C)C>>[C:77]([CH2:35][O:34][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=2)[CH:11]([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH:10]1[CH2:47][C:68]([OH:70])=[O:69])([OH:80])=[O:75]

Komponenten

5

Edukt 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 187038763-(4Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylateHCID 187038773-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid

Produkt 1

HCID 101663713-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acidAusbeute 84 %

Versuchsvorschrift

(1RS,2SR, 3RS)-3-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid. A solution of methyl (1RS, 2RS, 3RS)-3-(4methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (2.42 g, 4.6 mmol) in isopropyl alcohol (30 ml) with aqueous NaOH (8 ml of 5 N solution) was refluxed for 4 h. The resultant mixture was partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O then brine, dried (Na2SO4) and solvent removed in vacuo to afford the title compound as a colorless oil (1.98 g, 84%).

Aufarbeitung

  1. customThe resultant mixture was partitioned between EtOAc and 3N HCl
  2. extractionThe organic extract
  3. washwas washed with H2O
  4. dry with materialbrine, dried (Na2SO4) and solvent
  5. customremoved in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8b7f74c232c045a1ba16ce907826b12c
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271399B1

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