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

HRID 22586

Reaktionsgleichung

Reaktionsgleichung von HRID 22586
[CH:1](=O)[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.[SH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].C[Si](Cl)(C)C>C(Cl)(Cl)Cl>[CH:5]([C:4]1[CH:3]=[C:2]([CH:1]([S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[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 (40 g, 0.3 mol.) in chloroform (400 mL) and methyl 3-mercaptopropanoate (68 mL, 0.6 mol.) was added dropwise trimethylsilyl chloride (48 mL, 0.38 mol.) over 30 min. The reaction mixture was stirred at R.T. for 2 hours. The reaction was quenched with 25% aq. NH4OAc, extracted with ethyl acetate dried and evaporated. Flash chromatography of the residue afforded 50 gl of the title compound.

Aufarbeitung

  1. customThe reaction was quenched with 25% aq. NH4OAc
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-92e9c016c1de419ea0a48330884174ff
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428171

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