Water → 3-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxypyridine

HRID 70585Notes

Reaction equation

HRID 70585 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.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([C:46]([C:48]2[CH:53]=[CH:52][C:51]([S:54][CH3:55])=[CH:50][CH:49]=2)=O)=[N:42][C:43]=1[O:44][CH3:45].O>O1CCCC1>[Cl:37][C:38]1[C:43]([O:44][CH3:45])=[N:42][C:41](/[C:46](/[C:48]2[CH:53]=[CH:52][C:51]([S:54][CH3:55])=[CH:50][CH:49]=2)=[CH:17]/[CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 22315319(Cyclopentylmethyl)triphenylphosphonium iodideHCID 58452560(5-Chloro-6-methoxypyridin-2-yl)[4-(methylsulfanyl)phenyl]methanone

Product 1

HCID 674012323-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxypyridineYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithiumhexamethyldisilazide in tetrahydrofuran (1 M, 5.22 mL) was added to a solution of (cyclopentylmethyl)triphenylphosphonium iodide (described in WO 2001044216) (2.46 g) in tetrahydrofuran (20 mL) in a nitrogen atmosphere under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was ice-cooled again and a solution of (5-chloro-6-methoxypyridin-2-yl)[4-(methylsulfanyl)phenyl]methanone obtained in Reference Example 1-1 (1.0 g) in tetrahydrofuran (10 mL) was added, after which the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:hexane=1:1) to give 3-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxypyridine (710 mg, 58%) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooled again
  3. additionwas added
  4. stirringafter which the mixture was stirred at room temperature for one hour
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was then evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform:hexane=1:1)

Sources & evidence

ORD record
ord-421e23c2b0864b28a57cf12426a25013
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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