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

HRID 70585노트

반응식

HRID 70585 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-421e23c2b0864b28a57cf12426a25013
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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