Sodium Bicarbonate → 3a-Methyl-5,6-epoxy-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione
Reaktionsgleichung
[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[C:9]([CH2:10][CH2:11]2)=[C:8]([CH2:12][CH2:13][C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)[C:7](=[O:20])[CH2:6][O:5]1.C(=O)(O)[O-:26].[Na+]>ClCCl>[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[CH:9]3[CH:10]([O:26][C:8]3([CH2:12][CH2:13][C:14]3([CH3:19])[O:15][CH2:16][CH2:17][O:18]3)[C:7](=[O:20])[CH2:6][O:5]1)[CH2:11]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -30 °C
Versuchsvorschrift
A solution of 70% meta-perobenzoic acid (939 mg, 3.8 mmol) in dichloromethane (20 mL) was added dropwise to a suspension of 3a-methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione (800 mg, 2.53 mmol) and sodium bicarbonate (213 mg, 3.8 mmol) in dichloromethane (51 mL) at −30° C. The resulting mixture was stirred at −30° C. for 16 h. The reaction was then quenched with saturated solution of sodium thiosulfate. The resulting mixture was treated with saturated sodium carbonate solution and then extracted with dichloromethane (2×50 mL). The combined organic layer was dried with magnesium sulfate. The resulting solution was filtered and concentrated to yield the title compound as a white foam.
Aufarbeitung
- customThe reaction was then quenched with saturated solution of sodium thiosulfate
- additionThe resulting mixture was treated with saturated sodium carbonate solution
- extractionextracted with dichloromethane (2×50 mL)
- dry with materialThe combined organic layer was dried with magnesium sulfate
- filtrationThe resulting solution was filtered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-b3dfd468cd5d4409b9566c3dc1c77e5c
- Quelldatensatz
- uspto-grants-2010_07
- Patentnummer
- US07763648B2
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