Acetic Acid → HCID 15728609, compound

HRID 1197051Notes

Reaction equation

HRID 1197051 reaction equation
[CH3:1][S-:2].[Na+].C(O)(=O)C.C(N(CC)CC)C.[O:15]1[CH:20]2[CH:16]1[C:17](=O)[CH2:18][C:19]2([OH:32])[CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.O>[CH3:1][S:2][C:17]1[C:16](=[O:15])[CH2:20][C:19]([OH:32])([CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 15728606HCID 15728606, compound

Product 1

HCID 15728609HCID 15728609, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1.5 g of sodium thiomethoxide dissolved in 80 ml of methanol was added 1.8 ml of acetic acid under ice-cooling and stirring. After the mixture was stirred for 5 minutes, 4.8 ml of triethylamine was added, and the solution of 1.38 g of 2,3-epoxy-4-hydroxy-4-(4-phenoxybutyl)cyclopentanone obtained in Example 51 dissolved in 20 ml of methanol was added. After the mixture was stirred for 4 hours, water was added and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 1.39 g (yield 83%) of 2-methylthio-4-hydroxy-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. temperaturecooling
  2. stirringAfter the mixture was stirred for 5 minutes
  3. additionwas added
  4. stirringAfter the mixture was stirred for 4 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-7c82aa8b245b46e084502e7fb470bf39
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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