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

HRID 22581

Reaction equation

HRID 22581 reaction equation
[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]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 18050Methyl 3-mercaptopropionateHCID 34777Isophthalaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of isophthalaldehyde (5.4 g) in CHCl3 (50 ml) and methyl 3 -mercaptopropanoate (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 ethylacetate. Flash chromatography of the residue using 1:1 ethylacetate hexane afforded the title compound.

Workup

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

Sources & evidence

ORD record
ord-c469832204c34d678b6a98d513e0690c
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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