Tin atom → 4-Mercapto-2-propylphenoxy-acetic acid ethyl ester

HRID 985041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985041
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=O)=O)=[CH:9][C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[Sn].Cl.O1CCOCC1>C(O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]

Komponenten

5

Edukt 3

HCID 5352426Tin atomHCID 204431481,4-Dioxane hydrochlorideHCID 207681244-Chlorosulfonyl-2-propylphenoxy-acetic acid ethyl ester

Produkt 1

HCID 207681114-Mercapto-2-propylphenoxy-acetic acid ethyl esterAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Compound 4.3 (43.27 g, 134.9 mmol) was dissolved in ethanol (168.6 mL). To the solution was added tin (80.1 g, 674.5mmol) and the reaction was stirred at room temperature for 15 min., then cooled to 0° C. To the reaction was added 4N HCl/dioxane solution (168.6 mL, 674.5 mmol) dropwise at 0° C. Then the reaction was refluxed for 3.5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and filtered to remove insoluble materials and the filtrate was concentrated in vacuo to give the residue. The resulting residue was purified using silica gel column chromatography (hexane/EtOAc=10/1) to give 4.4 (27.2 g). 1H NMR (400 MHz) (CDCl3) δ 7.13 (1H, d, J=2.3 Hz); 7.09 (1H, dd, J=2.4, 8.4 Hz); 6.60 (1H, d, J=8.4 Hz); 4.59 (2H, s); 4.25 (2H, q, J=7.1 Hz); 3.32(1H, s); 2.63-2.55 (2H, m); 1.68-1.57 (2H, m); 1.28 (3H, t, J=7.1 Hz); 0.95 (3H, t, J=7.4 Hz).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. temperatureThen the reaction was refluxed for 3.5 h
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. filtrationfiltered
  6. customto remove insoluble materials
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto give the residue
  9. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-95625ed82073459093237844eabea4fc
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869975B2

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