Sodium Hydroxide → HCID 178528004, compound

HRID 259292Notes

Reaction equation

HRID 259292 reaction equation
[CH:1]1([SH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O1CCOCC1.Cl[CH2:16][C:17]([C-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1)=O.[CH-:24]1[CH:28]=[CH:27][CH:26]=[CH:25]1.[Fe+2:29]>O>[CH:19]1([CH2:17][C:16]([C-:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)=[S:6])[CH2:23][CH2:22][CH2:21][CH2:20]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:29]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 15510CyclopentanethiolHCID 312751,4-DioxaneHCID 178520780HCID 178520780, compound

Product 1

HCID 178528004HCID 178528004, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Cyclopentylmercaptan (ca 1.5g, 0.015M) was added to a solution of sodium hydroxide (0.6g, 0.015M) in water (3 ml). Dioxan (45 ml) was added, followed by chloroacetylferrocene (3.9g, 0.015M), and the mixture was heated at 100° for 2 hours with stirring. On cooling, water was added to the reaction mixture which was then extracted with chloroform. The organic layer was washed with dilute sodium hydroxide and water before it was dried over anhydrous magnesium sulphate and evaporated to an oil on a rotary evaporator. The product was isolated after column chromatography on silica gel using gradient elution with 1-21/2% (v/v) ethyl acetate in petroleum ether (60-80). Orange needles (0.40g) of the title compound were obtained mp = 78°-9°.

Workup

  1. temperaturethe mixture was heated at 100° for 2 hours
  2. temperatureOn cooling
  3. extractionwas then extracted with chloroform
  4. washThe organic layer was washed with dilute sodium hydroxide and water before it
  5. dry with materialwas dried over anhydrous magnesium sulphate
  6. customevaporated to an oil on a rotary evaporator
  7. customThe product was isolated after column chromatography
  8. washon silica gel using gradient elution with 1-21/2% (v/v) ethyl acetate in petroleum ether (60-80)

Sources & evidence

ORD record
ord-39a95ddbef22412294f82047160e0103
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Reaction notes

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