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

HRID 1073863

反応式

HRID 1073863 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ac034a99f454a8ab04abb67aaf2034c
出典データセット
uspto-grants-1990_11
特許番号
US04971982

関連ノート

読み込み中…