Pyridine → HCID 15728541, compound

HRID 1197056Notes

Reaction equation

HRID 1197056 reaction equation
[CH3:1][S:2][C:3]1[C:4](=[O:32])[CH:5]([CH:21]([OH:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([O:8][Si](C)(C)C)[CH:7]=1.N1C=CC=CC=1.N1C=CC=CC=1.F.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:1][S:2][C:3]1[C:4](=[O:32])[CH:5]([CH:21]([OH:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:6]([OH:8])([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 15728539HCID 15728539, compound

Product 1

HCID 15728541HCID 15728541, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 63 mg of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-octyl-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 71 dissolved in 6 ml of acetonitrile was added 130 μl of pyridine. A hydrogen fluoride-pyridine solution (260 μl) was added, and the mixture was stirred for 18 hours. The reaction 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 column chromatography to give 22 mg (yield 41%) of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-hydroxy-4-octyl-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-49e72468685547a5b38d374b66069f95
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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