Cyclohexanethiol → HCID 178520905, compound

HRID 259293Notes

Reaction equation

HRID 259293 reaction equation
[C:1]([C-:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)(=[O:4])[CH:2]=[CH2:3].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].[CH:16]1([SH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C.C(Cl)(Cl)Cl>[CH:16]1([S:22][CH2:3][CH2:2][C:1]([C-:5]2[CH:9]=[CH:8][CH:7]=[CH:6]2)=[O:4])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

5

Reactant 2

HCID 15290CyclohexanethiolHCID 178458219HCID 178458219, compound

Product 1

HCID 178520905HCID 178520905, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of acryloyl ferrocene (2.16g) and cyclohexylmercaptan (1.16g) in ethanol (50 ml) was set aside at ambient temperature for 24 hours. Evaporation of the ethanol gave an oil which was dissolved in chloroform (100 ml). The chloroform solution was washed successively with aqueous sodium hydroxide and water, dried over sodium sulphate and evaporated affording crude product. This was chromatographed through a silica-gel column (66g) 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, washed well with petroleum ether and dried giving the title compound, m.p. 46.5°-48.5°to C.

Workup

  1. customEvaporation of the ethanol
  2. customgave an oil which
  3. washThe chloroform solution was washed successively with aqueous sodium hydroxide and water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customaffording crude product
  7. customThis was chromatographed through a silica-gel column (66g)
  8. custom1% ethyl acetate/petroleum ether (60°-80°)
  9. customThis afforded an oil which
  10. customcrystallised
  11. temperatureon cooling
  12. filtrationThe solid was filtered off
  13. washwashed well with petroleum ether
  14. customdried

Sources & evidence

ORD record
ord-279312905a8a46a09bbd32616afd82c5
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Reaction notes

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