Ammonium Chloride → 1-(2-Methoxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol

HRID 1073863

반응식

HRID 1073863 반응식
Br[CH:2]=[C:3]([CH3:5])[CH3:4].[Mg].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])=[O:14].[Cl-].[NH4+]>O1CCCC1>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=1)([OH:14])[CH:2]=[C:3]([CH3:5])[CH3:4]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 985601-Bromo-2-methyl-1-propeneHCID 6039422-(2-Methoxybenzoyl)pyridineHCID 5462224Magnesium

생성물 1

HCID 198955961-(2-Methoxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol수율 60.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

43.84 g of 1-bromo-2-methylprop-1-ene in 150 ml of tetrahydrofuran were added dropwise to 9.8 g of magnesium in 50 ml of tetrahydrofuran while heating at reflux. After 1 hour the mixture was allowed to cool to room temperature, whereupon 47.7 g of 2-methoxyphenyl 2-pyridyl ketone in 200 ml of tetrahydrofuran were added slowly. After stirring for 2 hours at room temperature 200 ml of saturated ammonium chloride were added and the mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:6) followed by ethyl acetate/petroleum ethyl (1:4) for the elution to yield 36.6 g of 1-(2-methoxyphenyl)-3-methyl-1-(2-pyridyl) -2-buten-1-ol in the form of an oil.

후처리

  1. temperaturewhile heating
  2. temperatureat reflux
  3. additionwere added slowly
  4. additionwere added
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washfollowed by ethyl acetate/petroleum ethyl (1:4) for the elution

출처 및 근거

ORD 기록
ord-4ac034a99f454a8ab04abb67aaf2034c
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

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