Sodium Hydroxide → HCID 178520905, compound

HRID 259289Notes

Reaction equation

HRID 259289 reaction equation
[OH-].[Na+].[CH:3]1([SH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.O1CCOCC1.Cl[CH2:17][CH2:18][C:19]([C-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1)=[O:20].[CH-:26]1[CH:30]=[CH:29][CH:28]=[CH:27]1.[Fe+2:31]>O>[CH:3]1([S:9][CH2:17][CH2:18][C:19]([C-:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)=[O:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH-:26]1[CH:30]=[CH:29][CH:28]=[CH:27]1.[Fe+2:31]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 15290CyclohexanethiolHCID 312751,4-DioxaneHCID 178520645HCID 178520645, compound

Product 1

HCID 178520905HCID 178520905, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.25 mole) dissolved in minium water was treated with cyclohexylmercaptan (0.25 mole) and 700 ml dioxan. Chloropropionylferrocene (0.25 mole) was then added and the resulting mixture stirred on a steam bath for 3 hours. The mixture was diluted with water and extracted with chloroform. The organic liquors were washed successively with aqueous sodium hydroxide and water, dried and concentrated affording crude product. This was chromatographed through a silica gel column (20:1 ratio of silica to substrate) using initially 1% ethyl acetate/petroleum ether (60°-80°) then 3% ethyl acetate/petroleum ether as eluent. This afforded an oil which crystallised on cooling and trituration with petroleum ether. The solid was filtered off and washed with petroleum ether affording 3-(cyclohexylthio)propionyl ferrocene, mp 46.5°-48.5°, in 20% yield. Concentration of the petroleum ether liquors afforded a further 3% yield of product.

Workup

  1. extractionextracted with chloroform
  2. washThe organic liquors were washed successively with aqueous sodium hydroxide and water
  3. customdried
  4. concentrationconcentrated
  5. customaffording crude product
  6. customThis was chromatographed through a silica gel column (20:1 ratio of silica to substrate)
  7. custom1% ethyl acetate/petroleum ether (60°-80°)
  8. customThis afforded an oil which
  9. customcrystallised
  10. temperatureon cooling
  11. filtrationThe solid was filtered off
  12. washwashed with petroleum ether

Sources & evidence

ORD record
ord-25d7bd8e9c7146fd895b343b879a133b
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Reaction notes

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