Benzenesulfonyl hydrazide → Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoate

HRID 736491

Reaktionsgleichung

Reaktionsgleichung von HRID 736491
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][C:3]1=[CH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C1(S(NN)(=O)=O)C=CC=CC=1>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 65723Benzenesulfonyl hydrazideHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Produkt 1

HCID 22478914Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoateAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 260 (400 mg, 1.36 mmol) and benzenesulfonyl hydrazine (702 mg, 4.08 mmol) in DMF (7 ml) was stirred at 100° C. during 48 h. The solvent was evaporated and the residue was diluted in AcOEt, washed with NH4Cl sat., brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx)to afford the title compound 264 (170 mg, 42%) as a white solid. LRMS: 296.1 (Calc.); 297.0 (found).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was diluted in AcOEt
  3. washwashed with NH4Cl sat., brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx)to

Quellen und Nachweise

ORD-Eintrag
ord-1955c810a3794231b42d031e52a40e07
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595343B2

Verknüpfte Notizen

Wird geladen…