Cesium carbonate → HCID 71655300, Verbindung

HRID 270106

Reaktionsgleichung

Reaktionsgleichung von HRID 270106
[N+](C1C=C(S(O[CH2:14][C@@H:15]2[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.[OH:18][C:19]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:29][C:27]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:18][CH2:14][C@@H:15]2[CH2:17][O:16]2)[CH:28]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Produkt 1

HCID 71655300HCID 71655300, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (777.7 mg, 3.0 mmol), methyl 2-hydroxy-4-methylbenzoate ((498.5 mg, 3.0 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in petroleum spirit) to give the subtitled compound (500 mg).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-20% ethyl acetate in petroleum spirit)

Quellen und Nachweise

ORD-Eintrag
ord-5da029fadcd84547a917c3e533b8f518
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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