Hydrochloric Acid → HCID 18365658, compound

HRID 1728965Notes

Reaction equation

HRID 1728965 reaction equation
C[Mg]Br.Cl.[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1.[CH2:24](OCC)[CH3:25]>>[CH3:18][C:13]1[CH2:11][C:5]2[C:10]([CH:14]=1)=[C:9]([CH2:24][CH3:25])[CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 178418573HCID 178418573, compound

Product 1

HCID 18365658HCID 18365658, compound

Procedure

140 ml (420 mmol) of a 3 M ethereal methylmagnesium bromide solution were added to a solution of 22.4 g (140 mmol) of a3 in 500 ml of diethyl ether at room temperature under Ar protection in the course of 1 hour. The mixture was then stirred under reflux at room temperature for another 2 hours, and was stirred at room temperature for a further 15 hours. The mixture was poured onto ice acidified with HCl, and extracted with ether. After the extract had been dried over sodium sulfate, the solvent was stripped off. The yellow oil which remained (20.3 g) was taken up in 800 ml of analytical grade toluene, 2.2 g (11.5 mmol) of p-toluenesulfonic acid hydrate were added and the mixture was refluxed for 45 minutes. After cooling, the solution was washed several times with water, dried over sodium sulfate and evaporated. The residue was chromatographed on 620 g of silica gel 60.5.5 g (25%) of the indene a4 (yellowish oil) could be eluted with hexane/methylene chloride (20:1). Still unused starting material a3 could be recovered with hexane/ethyl acetate (9:1).

Workup

  1. stirringwas stirred at room temperature for a further 15 hours
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ether
  4. dry with materialAfter the extract had been dried over sodium sulfate
  5. additionwere added
  6. temperaturethe mixture was refluxed for 45 minutes
  7. temperatureAfter cooling
  8. washthe solution was washed several times with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe residue was chromatographed on 620 g of silica gel 60.5.5 g (25%) of the indene a4 (yellowish oil)
  12. washcould be eluted with hexane/methylene chloride (20:1)
  13. customcould be recovered with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-e0abd6483b3a4a25a4fe8438428e0c66
Source dataset
uspto-grants-1994_07
Patent number
US05329033

Reaction notes

Loading…