Water → Methyl 4-[(phenylmethylene)amino]-6-(trimethylsilyl)-5-hexynoate

HRID 1380485ノート

反応式

HRID 1380485 の反応式
C([Li])CCC.[CH:6](=[N:13][CH2:14][C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].O>CCCCCC.O1CCCC1>[CH3:20][Si:17]([CH3:19])([CH3:18])[C:16]#[C:15][CH:14]([N:13]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:23][CH2:22][C:21]([O:25][CH3:26])=[O:24]

参加物

7

反応物 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 12918300HCID 12918300、化合物HCID 178418339Butyllithium

生成物 1

HCID 13780253Methyl 4-[(phenylmethylene)amino]-6-(trimethylsilyl)-5-hexynoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

53.6 ml of a 1.6M solution of n-butyllithium in hexane was added drop-by-drop over 20 minutes to a solution of 18.0 g of 1B in 700 ml of dry tetrahydrofuran at -70° C. The resulting mixture was stirred for 20 minutes at -70° C., when 7.2 g of freshly distilled methyl acrylate was added over 14 minutes. The resulting mixture was stirred for 30 minutes at -70° C., when 16.5 ml of water was added drop-by-drop. The resulting mixture was allowed to warm slowly to room temperature; the solvent was evaporated; the residue was diluted with water and the resulting mixture was extracted with ether. The ether extract was washed with brine, dried (Na2SO4), filtered and the solvent was evaporated. The residue (a dark thick oil) was distilled in a Kugelrohr apparatus to give methyl 6-(trimethylsilyl)-4-(benzylideneamino)-5-hexynoate (3A), b.p.: 140°-142° C. (0.01 Torr.).

後処理

  1. stirringThe resulting mixture was stirred for 30 minutes at -70° C.
  2. temperatureto warm slowly to room temperature
  3. customthe solvent was evaporated
  4. additionthe residue was diluted with water
  5. extractionthe resulting mixture was extracted with ether
  6. extractionThe ether extract
  7. washwas washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. distillationThe residue (a dark thick oil) was distilled in a Kugelrohr apparatus

出典と根拠

ORDレコード
ord-e11d15204bd94fcfb6e119ee36644b5a
出典データセット
uspto-grants-1986_04
特許番号
US04582529

反応ノート

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