Sodium Iodide → HCID 23130569, compound

HRID 2080090Notes

Reaction equation

HRID 2080090 reaction equation
[I-].[Na+].C[Si](Cl)(C)C.[O:8]1CCO[CH:9]1[C:13]1[S:17][C:16]([CH:18]([C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)O)=[CH:15][CH:14]=1.[OH-].[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O.C(OCC)(=O)C>[CH3:25][C:22]1[S:21][C:20]([CH2:18][C:16]2[S:17][C:13]([CH:9]=[O:8])=[CH:14][CH:15]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 23130404HCID 23130404, compound

Product 1

HCID 23130569HCID 23130569, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium iodide (6.4 g, 42.6 mmol) and trimethylsilyl chloride (4.6 g, 42.6 mmol) were suspended in acetonitrile (100 mL) on an ice bath, and (5-[1,3]dioxolane-2-ylthiophen-2-yl)-(5-methyl-thiophen-2-yl)-methanol described in Preparation Example 65 (2.0 g, 7.09 mmol) was added dropwise. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. A solution obtained by dissolving an aqueous solution of 2N sodium hydroxide (10.6 mL) and sodium thiosulfate pentahydrate (530 mg, 2.13 mmol) in water (5 mL) was added to the reaction solution that had been cooled on an ice bath, and the solution was stirred. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was concetrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (790 mg, 3.56 mmol, 50.2%) was obtained as a brown oil.

Workup

  1. additionwas added dropwise
  2. additionAfter dropwise addition
  3. customwas gradually allowed to room temperature
  4. customA solution obtained
  5. additionwas added to the reaction solution that
  6. temperaturehad been cooled on an ice bath
  7. customwas then partitioned
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-a2a14212da70472b946aad7323dbac02
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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