Acetic Acid → HCID 15728609, compound

HRID 1197050Notes

Reaction equation

HRID 1197050 reaction equation
[CH3:1][S-:2].[Na+].C(O)(=O)C.[O:8]1[CH:13]2[CH:9]1[C:10](=O)[CH2:11][C:12]2([O:25][Si](C)(C)C)[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>CO.C(N(CC)CC)C>[CH3:1][S:2][C:10]1[C:9](=[O:8])[CH2:13][C:12]([OH:25])([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 15728607HCID 15728607, compound

Product 1

HCID 15728609HCID 15728609, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 25 mg of sodium thiomethoxide dissolved in methanol, 51 μl of acetic acid was added, and the mixture was stirred for 10 minutes. Triethylamine (170 μl ) was then added, and after the mixture was stirred for 10 minutes, a solution of 16 mg of 2,3-epoxy-4-trimethylsilyloxy-4-(4-phenoxybutyl)cyclopentanone obtained in Example 51 in 3 ml of methanol was added and the mixture was stirred for 5 hours. Then saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. After filtration and concentration, the concentrate was subjected to silica gel column chromatography to obtain 7.1 mg (yield 51%) of 2-methylthio-4-hydroxy-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. stirringafter the mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred for 5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-0051157cc5cd4340af87c29df045fd3e
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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