Benzaldehyde → Stilbene oxide

HRID 1941485

Reaktionsgleichung

Reaktionsgleichung von HRID 1941485
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(SC)=CC=1.[C:19]1([CH:25]=[N+]=[N-])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C([O-])(=O)C.[Rh+2].C([O-])(=O)C.ClCCl>[C:19]1([CH:25]2[O:8][CH:1]2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 158851-Methoxy-4-(methylthio)benzeneHCID 136601Benzene, (diazomethyl)-

Produkt 1

HCID 28649Stilbene oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21674Acetic acid, rhodium(2+) saltKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of rhodium (II) acetate (0.0021 g), dichloromethane (4 ml) and benzaldehyde (0.051 ml) was added 1-methoxy-4-methylthiobenzene (0.0036 ml). To this mixture was added, with stirring, a solution of phenyldiazomethane (1 mmol in tert-butylmethyl ether (8 ml)) over 19 hours. The reaction mixture was stirred or a further 5 hours after which the mixture was allowed to stand at room temperature for 2 days. The solvent was removed in vacuo and the residue chromatographed on silica using dichloromethane:hexane 2:3 as eluant. The title compound was obtained as a colourless oil (0.0713 g, 22.6% yield).

Aufarbeitung

  1. additionTo this mixture was added
  2. stirringThe reaction mixture was stirred or a further 5 hours after which the mixture
  3. customThe solvent was removed in vacuo
  4. customthe residue chromatographed on silica

Quellen und Nachweise

ORD-Eintrag
ord-0dbe1c655d8e40b7be2f8453fee14b0f
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703246

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