Trimethylsilyl iodide → Ethanethioic acid S-[tetrahydro-5-(iodomethyl)-3-thienyl]ester

HRID 54785Notes

Reaction equation

HRID 54785 reaction equation
C1(CO[CH2:9][CH:10]2[S:14][CH2:13][CH:12]([S:15][C:16](=[O:18])[CH3:17])[CH2:11]2)C=CC=CC=1.C[Si]([I:23])(C)C>C(Cl)(Cl)Cl>[I:23][CH2:9][CH:10]1[S:14][CH2:13][CH:12]([S:15][C:16](=[O:18])[CH3:17])[CH2:11]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 54092544HCID 54092544, compound

Product 1

HCID 54241013Ethanethioic acid S-[tetrahydro-5-(iodomethyl)-3-thienyl]ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 0° C. mixture, under argon, of 0.44 g of product from Example 139 in 5 ml of dry chloroform is treated with 0.55 ml of trimethylsilyl iodide. The reaction is stirred, in the dark, for 2 hours. The reaction is quenched with 100 ml of saturated sodium sulfite, extracted with methylene chloride and the layers separated. The organic layer is dried, filtered and concentrated in vacuo. The residue is purified by. chromatography (silica gel: 0-100% methylene chloride/hexane) to give 0.31 g of the product.

Workup

  1. customThe reaction is quenched with 100 ml of saturated sodium sulfite
  2. extractionextracted with methylene chloride
  3. customthe layers separated
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by

Sources & evidence

ORD record
ord-2bb411a2cc9c4bd1ba92e6db2f37a220
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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