2-Chloro-4-(4-methoxyphenyl)pyridine → 4-(4-Methoxyphenyl)-2-methylpyridine

HRID 657662노트

반응식

HRID 657662 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:16][Mg]Br>O1CCCC1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:16])[CH:7]=2)=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 534408782-Chloro-4-(4-methoxyphenyl)pyridineHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 233717804-(4-Methoxyphenyl)-2-methylpyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 2-chloro-4-(4-methoxyphenyl)pyridine (660 mg) and bis(triphenyl-phosphine)nickeldichloride (200 mg) in anhydrous tetrahydrofuran (7.5 mL) is cooled to a temperature close to 0° C. A solution of methylmagnesiumbromide in tetrahydrofuran (2.6 M, 2 mL) is added slowly. The mixture is stirred at room temperature for two hours, concentrated under reduced pressure and dissolved in methyl tert-butyl ether (10 mL). Alkaloids are extracted with a 3N aqueous solution of hydrochloric acid (3 times 10 mL). Extracts are pooled, alkalinised and back extracted with methyl tert-butyl ether (3 times 20 mL) and dichloromethane (30 mL). Organic phases are dried over magnesium sulphate, concentrated under reduced pressure and purified over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5). Fraction containing the expected product are pooled and concentrated under reduced pressure to give 385 mg of 4-(4-methoxyphenyl)-2-methylpyridine as a clear brown powder used without further purification.

후처리

  1. temperatureis cooled to a temperature
  2. customclose to 0° C
  3. concentrationconcentrated under reduced pressure
  4. dissolutiondissolved in methyl tert-butyl ether (10 mL)
  5. extractionAlkaloids are extracted with a 3N aqueous solution of hydrochloric acid (3 times 10 mL)
  6. extractionback extracted with methyl tert-butyl ether (3 times 20 mL) and dichloromethane (30 mL)
  7. dry with materialOrganic phases are dried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. custompurified over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5)
  10. additionFraction containing the expected product
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-305abb4e9af24ae1bb743ac7acdfa6c5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076329B2

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