Methyl iodide → HCID 20069480, compound

HRID 981427Notes

Reaction equation

HRID 981427 reaction equation
[CH3:1][CH:2]1[CH2:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[C:3]1=[O:10].[C:11]([O-])(C)(C)C.[K+].CI>C(O)(C)(C)C>[CH3:1][C:2]1([CH3:11])[CH2:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[C:3]1=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 12564771HCID 12564771, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20069480HCID 20069480, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of 28.6 g of 5,6-dihydro-5-methyl-4H-cyclopenta[b]thiophen-4-one in 210 ml of tert.-butanol is added dropwise at from +25° to +30° C. to a solution of 23.1 g of potassium tert.-butanolate in 250 ml of tert.-butanol. The dark reddish-brown solution is stirred for 1.5 hours, and then 12.9 ml of methyl iodide are added. After stirring for 1 hour, the reddish-brown suspension is filtered and the filtrate is concentrated by evaporation. After distillation of the residue there are obtained 26.0 g of 5,6-dihydro-5,5-dimethyl-4H-cyclopenta[b]thiophen-4-one in the form of a colourless oil having a boiling point of 43° C. at 0.03 mbar.

Workup

  1. stirringAfter stirring for 1 hour
  2. filtrationthe reddish-brown suspension is filtered
  3. concentrationthe filtrate is concentrated by evaporation
  4. distillationAfter distillation of the residue there

Sources & evidence

ORD record
ord-ec7e0761d14f476995acf17b6a42089e
Source dataset
uspto-grants-1991_02
Patent number
US04992090

Reaction notes

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