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

HRID 1290396Notes

Reaction equation

HRID 1290396 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 chromatography (silica gel: 0 -100% methylene chloride/hexane)

Sources & evidence

ORD record
ord-de4b2ab3c9ff4044ae5dd833a440b9a6
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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