Water → (Z)-6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxy-3-methylpyridine

HRID 70617Notes

Reaction equation

HRID 70617 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[I-].[CH:12]1([CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH3:37][O:38][C:39]1[N:44]=[C:43]([C:45]([C:47]2[CH:52]=[CH:51][C:50]([S:53][CH3:54])=[CH:49][CH:48]=2)=O)[CH:42]=[CH:41][C:40]=1[CH3:55].O>O1CCCC1>[CH:12]1(/[CH:17]=[C:45](\[C:43]2[N:44]=[C:39]([O:38][CH3:37])[C:40]([CH3:55])=[CH:41][CH:42]=2)/[C:47]2[CH:52]=[CH:51][C:50]([S:53][CH3:54])=[CH:49][CH:48]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 22315319(Cyclopentylmethyl)triphenylphosphonium iodideHCID 58452596(6-Methoxy-5-methylpyridin-2-yl)[4-(methylsulfanyl)phenyl]methanone

Product 1

HCID 67396349(Z)-6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxy-3-methylpyridineYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithiumhexamethyldisilazide in tetrahydrofuran (1 M, 5.5 mL) was added to a solution of (cyclopentylmethyl)triphenylphosphonium iodide (1.73 g, 3.66 mmol) in tetrahydrofuran (5 mL) in a nitrogen atmosphere under ice-cooling, and the mixture was stirred under ice-cooling for one hour. A solution of (6-methoxy-5-methylpyridin-2-yl)[4-(methylsulfanyl)phenyl]methanone obtained in Reference Example 1-36 (1.0 g) in tetrahydrofuran (2.5 mL) was added to the reaction solution under ice-cooling, and the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:hexane=1:9→1:2) to give (Z)-6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxy-3-methylpyridine (493 mg, 40%) as a more polar product.

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. additionwas added to the reaction solution under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 16 hours
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform:hexane=1:9→1:2)

Sources & evidence

ORD record
ord-8455e543dca0450485de52618324c5f9
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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