Diisopropylamine → 4,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanol

HRID 242410

반응식

HRID 242410 반응식
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([O:21][CH3:22])[CH:15]=1.ClC1C(Cl)=CN=C(OC)C=1[Li].[CH3:34][O:35][C:36]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[C:40]([CH3:48])[C:37]=1[CH:38]=[O:39]>O1CCCC1.O>[CH3:34][O:35][C:36]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[C:40]([CH3:48])[C:37]=1[CH:38]([C:15]1[C:16]([O:21][CH3:22])=[N:17][CH:18]=[C:19]([Cl:20])[C:14]=1[Cl:13])[OH:39]

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 230825824,5-Dichloro-2-methoxypyridineHCID 178418339ButyllithiumHCID 178506770HCID 178506770, 화합물

생성물 1

HCID 230826084,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanol수율 51%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

15.1 ml of n-butyllithium (1.57 mol/l hexane solution) was dropwise added at −20° C. to a solution having 2.40 g (23.7 mmol) of diisopropylamine dissolved in 30 ml of tetrahydrofuran, followed by stirring for 1 hour. The solution was cooled to −78° C., and a solution having 4.22 g (23.6 mmol) of 4,5-dichloro-2-methoxypyridine obtained in Step (e) dissolved in 20 ml of tetrahydrofuran was added, followed by stirring for 2 hours to prepare 4,5-dichloro-2-methoxy-3-pyridyllithium. Then, to this solution, a solution having 5.00 g (23.8 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 20 ml of tetrahydrofuran was added, followed by stirring for 30 minutes. 50 ml of water was added to the mixture to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. After extraction with ethyl ether, the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography to obtain 4.66 g (yield: 51%) of (2,3,4-trimethoxy-6-methylphenyl)(4,5-dichloro-2-methoxy-3-pyridyl)methanol.

후처리

  1. additionwas added
  2. stirringby stirring for 2 hours
  3. additionwas added
  4. stirringby stirring for 30 minutes
  5. customto terminate
  6. customthe reaction, and tetrahydrofuran
  7. distillationwas distilled off under reduced pressure
  8. extractionAfter extraction with ethyl ether
  9. dry with materialthe organic layer was dried over sodium sulfate
  10. filtrationsubjected to filtration
  11. distillationthe solvent was distilled off under reduced pressure
  12. customfollowed by purification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-350328760e4c4c22b3bf252a51fa5b41
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653113B2

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