Pyridine → HCID 86745873, compound

HRID 1587135Notes

Reaction equation

HRID 1587135 reaction equation
N1C=CC=CC=1.N1C=CC=CC=1.F.[Si]([O:21][CH:22]([CH2:50][CH2:51][CH2:52][O:53][Si](C(C)(C)C)(C)C)/[CH:23]=[CH:24]\[CH:25]=[C:26]1[C:30](=[O:31])[C:29]([S:32][CH3:33])=[CH:28][C:27]1([CH2:39][CH2:40][CH2:41][CH2:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:34][Si](C)(C)C)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[OH:21][CH:22]([CH2:50][CH2:51][CH2:52][OH:53])/[CH:23]=[CH:24]\[CH:25]=[C:26]1[C:30](=[O:31])[C:29]([S:32][CH3:33])=[CH:28][C:27]1=[CH:39][CH2:40][CH2:41][CH2:42][O:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1.[OH:21][CH:22]([CH2:50][CH2:51][CH2:52][OH:53])/[CH:23]=[CH:24]\[CH:25]=[C:26]1[C:30](=[O:31])[C:29]([S:32][CH3:33])=[CH:28][C:27]1([OH:34])[CH2:39][CH2:40][CH2:41][CH2:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 86745874HCID 86745874, compound

Product 2

HCID 86745872HCID 86745872, compoundYield 20%HCID 86745873HCID 86745873, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 9 ml of pyridine dissolved in 50 ml of acetonitrile was added, 4.5 ml of hydrogen fluoride-pyridine solution, under ice-cooling and stirring. A solution of 1.41 g of 5-[(Z)-4,7-bis-(t-butyldimethylsilyloxy)-2-heptenylidene]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 570 in 15 ml of acetonitrile was added, and the mixture was stirred at 0° C. for 10 minutes, an at room temperature for 8 hours. The reaction mixture was poured onto saturated aqueous sodium hydrogencarbonate, and the mixture was extracted for 3 times with ethyl acetate. The organic layers were combined, washed once with saturated aqueous sodium hydrogencarbonate and twice with saturated aqueous sodium chloride. The product was dried over anhydrous magnesium sulfate, filtered and concentrated. The oily product obtained was subject to silica gel column chromatography to obtain 158 mg (yield 20%) of 5-[(Z)-4,7-dihydroxy-2-heptenylidene]-2-methylthio-4-(4-phenoxybutylidene)-2-cyclopentenone and 353 mg (yield 43%) of 5-[(Z)-4,7-dihydroxy-2-heptenylidene]-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 0° C. for 10 minutes
  3. extractionthe mixture was extracted for 3 times with ethyl acetate
  4. washwashed once with saturated aqueous sodium hydrogencarbonate and twice with saturated aqueous sodium chloride
  5. dry with materialThe product was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily product obtained

Sources & evidence

ORD record
ord-b747765d041d4101b2408f90b0c25fc2
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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