Water → 4-Phenylsulfonylphenylethyne

HRID 2376977

Reaktionsgleichung

Reaktionsgleichung von HRID 2376977
[C:1]1([S:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OCC)OCC)C(=O)C)=[N-].O>CO>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1)#[CH:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 144174774-(Benzenesulfonyl)benzaldehydeHCID 136104435(1Z)-1-diazo-1-diethoxyphosphorylpropan-2-one

Produkt 1

HCID 199393204-PhenylsulfonylphenylethyneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 4-(phenylsulfonyl)benzaldehyde (8 g, 32.5 mmol) and potassium carbonate (8.97 g, 65 mmol) in methanol (400 mL) was added diethyl (1-diazo-2-oxopropyl)phosphonate (8.6 g, 39 mmol). The reaction was stirred at room temperature for 3 days then poured into water (600 mL) and extracted with ethyl acetate (×3). The combined organic layers were dried and evaporated. The residue was purified by flash column chromatography on silica, eluting with 5% ethyl acetate/isohexane, to give 1-ethynyl-4-(phenylsulfonyl)benzene (3.3 g, 42%). δH (500 MHz, CDCl3): 7.94-7.88 (4H, m), 7.60-7.50 (5H, m), 3.23 (1H, s).

Aufarbeitung

  1. extractionextracted with ethyl acetate (×3)
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customThe residue was purified by flash column chromatography on silica
  5. washeluting with 5% ethyl acetate/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-bd1663955d9d4cf88849a93a36e9a7cd
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468393B2

Verknüpfte Notizen

Wird geladen…