Chlorotrimethylsilane → Dimethyl 3,3'-(((3-formylphenyl)methylene)bis(sulfanediyl))dipropanoate

HRID 1032321

Reaktionsgleichung

Reaktionsgleichung von HRID 1032321
[CH:1](=O)[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.C[Si](Cl)(C)C.[SH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>C(Cl)(Cl)Cl>[CH:5]([C:4]1[CH:3]=[C:2]([CH:1]([S:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[S:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:9]=[CH:8][CH:7]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 18050Methyl 3-mercaptopropionateHCID 34777Isophthalaldehyde

Produkt 1

HCID 10021188Dimethyl 3,3'-(((3-formylphenyl)methylene)bis(sulfanediyl))dipropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of isophthalaldehyde (5.4 g) in CHCl3 (50 mL) and methyl 3-mercaptopropionate (9.2 mL) was added dropwise trimethylsilylchloride (6.5 mL). The reaction mixture was stirred 1 hour at room temperature, quenched with aqueous NH4OAc (25%), and extracted with ethyl acetate. Flash chromatography of the residue using 1:1 ethyl acetate/ hexane afforded the title compound.

Aufarbeitung

  1. customquenched with aqueous NH4OAc (25%)
  2. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-293f25f37e6e4b30bf9d71d9a4471fe8
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04957932

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