Pyridine → HCID 53756288, compound

HRID 1197055Notes

Reaction equation

HRID 1197055 reaction equation
[Si]([O:8][CH:9]([CH2:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)[CH:10]=[CH:11][CH:12]([CH:14]1[C:18](=[O:19])[C:17]([S:20][CH3:21])=[CH:16][C:15]1([CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:22][Si](C)(C)C)[OH:13])(C(C)(C)C)(C)C.N1C=CC=CC=1.N1C=CC=CC=1.F.C(=O)([O-])O.[Na+]>C(#N)C>[OH:13][CH:12]([CH:14]1[C:18](=[O:19])[C:17]([S:20][CH3:21])=[CH:16][C:15]1([OH:22])[CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:11]=[CH:10][CH:9]([OH:8])[CH2:38][CH2:39][CH2:40][OH:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 53927203HCID 53927203, compound

Product 1

HCID 53756288HCID 53756288, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 270 mg of 5-[4,7-bis(t-butyldimethylsilyloxy)-1-hydroxy-2-heptenyl]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 62 dissolved in 15 ml of acetonitrile, 2 ml of pyridine was added. While stirring the mixture under ice-cooling, 1 ml of a hydrogen fluoride-pyridine solution was added and the mixture was stirred at 0° C.-room temperature for 16 hours. The mixture was poured onto saturated aqueous sodium hydrogencarbonate, 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 chromatography to give 114 mg (yield 71%) of 5-(1,4,7-trihydroxy-2-heptenyl)-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 0° C.-room temperature for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-2648d542e8374baeab2ae5b9f36cc8f6
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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