Methyl iodide → HCID 21533737, compound

HRID 1657465Notes

Reaction equation

HRID 1657465 reaction equation
ClC1C=CC(C2SC(CC(OC)=O)=CC=2)=CC=1.[H-].[Na+].CI.[CH3:22][C:23]([CH3:40])([C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)[C:24]([O:26]C)=[O:25]>O1CCOCC1>[CH3:22][C:23]([CH3:40])([C:28]1[S:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 13030795Methyl [5-(4-chlorophenyl)thiophen-2-yl]acetateHCID 53736027HCID 53736027, compound

Product 1

HCID 21533737HCID 21533737, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-p-chlorophenylthien-2-ylacetate (1 g.) was dissolved in dry dioxan (10 ml.). Sodium hydride (0.1 g.) was added, the mixture was stirred for 30 minutes, and methyl iodide (0.6 g.) was then added. The mixture was refluxed for 30 minutes, cooled, and further sodium hydride (0.1 g.) and methyl iodide (1.1 ml.) were added. The mixture was refluxed for 2 hours, cooled and evaporated in vacuo to give an oil which was chromatographed on a column of Florisil (column: 9 inches long × 1 inch diameter) which was eluted with a mixture of equal volumes of benzene and petroleum ether (b.p. 60°-80°C.). The first 350 ml. of eluate was evaporated in vacuo to give an oil. This oil, which was mainly methyl α,α-dimethyl-α-(5-p-chlorophenylthien-2-yl)acetate, was hydrolysed by conventional means and gave α,α -dimethyl-α-(5-p-chlorophenylthien-2yl)-acetic acid, m.p. 146°-148°C.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperaturecooled
  3. temperatureThe mixture was refluxed for 2 hours
  4. temperaturecooled
  5. customevaporated in vacuo
  6. customto give an oil which
  7. customwas chromatographed on a column of Florisil (column
  8. wash9 inches long × 1 inch diameter) which was eluted with a mixture of equal volumes of benzene and petroleum ether (b.p. 60°-80°C.)
  9. customof eluate was evaporated in vacuo
  10. customto give an oil

Sources & evidence

ORD record
ord-ec64d90f2e2c4407a2ea1df2a2935bee
Source dataset
uspto-grants-1976_06
Patent number
US03960893

Reaction notes

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