4-Toluenesulfonyl chloride → 1,3-Di-tert-butyl 2-diazopropanedioate
Reaktionsgleichung
[N-]=[N+:2]=[N-:3].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:16]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C>O.C(O)C>[C:21]([O:20][C:18](=[O:19])[C:17](=[N+:2]=[N-:3])[C:16]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:23])([CH3:24])[CH3:22]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of sodium azide (1.37 grams, 21.0 mmol), p-toluenesulfonyl chloride (4.0 grams, 21.0 mmol), and 70% aqueous ethanol (60 mL) was stirred at room temperature for 1 hour. Di-t-butyl malonate (4.48 mL, 20.0 mmol) and triethylamine (2.92 grams, 21.0 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours and then poured into deionized water (200 mL). The mixture was extracted with petroleum ether (2×200 mL). The extracts were combined and then washed with a saturated aqueous sodium chloride solution. The organic solution was dried using anhydrous magnesium sulfate, filtered, and concentrated to give 6.10 grams of di-t-butyl-2-diazomalonate as a yellow oil. IR(film): 2110 cm-1. Decomposition temperature: 178° C. (by DSC).
Aufarbeitung
- stirringThe reaction mixture was stirred at room temperature for 4 hours
- extractionThe mixture was extracted with petroleum ether (2×200 mL)
- washwashed with a saturated aqueous sodium chloride solution
- customThe organic solution was dried
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-22f09d8ab7294db2a4b4ed393167528d
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05756689
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