Triethylamine → 2-Methylthio-4-hydroxy-4-octyl-2-cyclopentenone

HRID 1587132Notes

Reaction equation

HRID 1587132 reaction equation
[CH3:1][S-:2].[Na+].C(N(CC)CC)C.[O:11]1[CH:16]2[CH:12]1[C:13](=O)[CH2:14][C:15]2([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[O:17][Si](C)(C)C.[Cl-].[NH4+]>CO>[CH3:1][S:2][C:13]1[C:12](=[O:11])[CH2:16][C:15]([OH:17])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 197605912,3-Epoxy-4-octyl-4-trimethylsilyloxycyclopentanone

Product 1

HCID 197605982-Methylthio-4-hydroxy-4-octyl-2-cyclopentenone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 910 mg of sodium thiomethoxide dissolved in 100 ml of methanol was stirred under ice-cooling and stirring for 15 minutes. Triethylamine (6 ml) was added, and after the mixture was stirred for 10 minutes, a solution of the above crude oil of 2,3-epoxy-4-octyl-4-trimethylsilyloxycyclopentanone in 15 ml of methanol was added dropwise. After the mixture was stirred for 6 hours, the reaction mixture was poured onto saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude oil of 2-methylthio-4-hydroxy-4-octyl-2-cyclopentenone.

Workup

  1. temperaturecooling
  2. stirringstirring for 15 minutes
  3. stirringafter the mixture was stirred for 10 minutes
  4. stirringAfter the mixture was stirred for 6 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-98f66a638aeb4251a8e8a428f841a5a0
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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