Hydrochloric Acid → HCID 178444360, compound

HRID 1285074Notes

Reaction equation

HRID 1285074 reaction equation
P(I)(I)P(I)I.[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH:22]3O[CH:23]3[CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH3:8].N1C=CC=CC=1.Cl>C(Cl)Cl>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][C@H:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 83484Hypodiphosphorous tetraiodide2×HCID 178440466HCID 178440466, compound

Product 1

HCID 178444360HCID 178444360, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 404.4 mg of diphosphorus tetraiodide in 5 ml of methylene chloride was treated dropwise while gassing with argon at room temperature within 5 minutes with a solution of 205 mg of 4-ethoxy-1-[trans-4-(1,2-epoxypentyl)cyclohexyl]benzene and 0.703 ml of pyridine in 8 ml of methylene chloride. The suspension was heated to reflux while stirring, a further 404.4 mg of diphosphorus tetraiodide being added after 2 hours. After stirring under reflux for a total of 19 hours, the reaction was interrupted and the mixture was treated with 1N hydrochloric acid and extracted three times with diethyl ether. The organic extracts were washed successively with 1N hydrochloric acid, sodium thiosulphate solution and water, dried over magnesium sulphate, filtered and evaporated. Chromatographic separation of the residue (0.2 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) as the eluent gave 120 mg of 4-ethoxy-1-[trans-4-(trans-1-pentenyl)cyclohexyl]benzene. After recrystallization from 10 ml of methanol, the product was obtained as white crystals of melting point (C-N) 32.2° C. and clearing point (N-I) 54.9° C.

Workup

  1. additionwas treated dropwise
  2. temperatureThe suspension was heated
  3. temperatureto reflux
  4. stirringAfter stirring
  5. temperatureunder reflux for a total of 19 hours
  6. extractionextracted three times with diethyl ether
  7. washThe organic extracts were washed successively with 1N hydrochloric acid, sodium thiosulphate solution and water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customChromatographic separation of the residue (0.2 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) as the eluent

Sources & evidence

ORD record
ord-50d3cdceabd44b6ca398f3fde210f7f3
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

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