Dimethyl Carbonate → (1S-trans)-Methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-oxo-5-propoxy-1H-indene-2-carboxylate
Reaktionsgleichung
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].C[O-].[Na+].[C:29](=O)([O:32]C)[O:30][CH3:31]>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[C@@H:11]3[C:29]([O:30][CH3:31])=[O:32])=[CH:9][C:4]=2[O:3][CH2:2]1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
A 100 mL three-necked flask under nitrogen was charged with (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one (1.5 g, 4.84 mmol), toluene (20 mL), 60% NaH suspension (213 mg, 5.3 mmol), NaOMe (288 mg, 5.3 =mmol), and dimethyl carbonate (2.5 mL, 29 mmol). The solution was warmed to 40 ° C. for 3 h, cooled to 0° C., quenched with 3 M AcOH (0.5 mL) and diluted with H2O (50 mL) and EtOAc (50 mL). The organic phase was washed with brine (50 mL), dried (MgSO4) and concentrated. The crude material was triturated with EtOAc/hexane (1:3, 50 mL) affording (1S-trans)-methyl 1-(1,3-benzodioxol-5-yl) -2,3-dihydro-3-oxo-5-propoxy-1H-indene-2-carboxylate as a pale yellow solid (710 mg, 73% yield).
Aufarbeitung
- temperaturecooled to 0° C.
- customquenched with 3 M AcOH (0.5 mL)
- additiondiluted with H2O (50 mL) and EtOAc (50 mL)
- washThe organic phase was washed with brine (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude material was triturated with EtOAc/hexane (1:3, 50 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-5d19cae0007f4f1d9986d8dfe8ec88bf
- Quelldatensatz
- uspto-grants-2002_03
- Patentnummer
- US06355813B1
Notizen zur Reaktion
Wird geladen…