Diisopropylamine → Ethyl 5-[1-(pyridin-3-yl)-1H-indol-3-yl]penta-2,4-dienoate

HRID 485334ノート

反応式

HRID 485334 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][CH2:14][O:15][C:16](/[CH:18]=[CH:19]/[CH2:20]P(OCC)(OCC)=O)=[O:17].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]([CH:44]=O)=[CH:36]2)[CH:30]=1>O1CCCC1.CCCCCC>[CH2:14]([O:15][C:16]([CH:18]=[CH:19][CH:20]=[CH:44][C:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:35]([C:31]2[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=2)[CH:36]=1)=[O:17])[CH3:13]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 13490349HCID 13490349、化合物HCID 178418339Butyllithium

生成物 1

HCID 54103669Ethyl 5-[1-(pyridin-3-yl)-1H-indol-3-yl]penta-2,4-dienoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

A solution of 1.27 ml of diisopropylamine in 25 ml of tetrahydrofuran is cooled to -65° under nitrogen and 5.7 ml of 1.6M n-butyllithium in hexane is added. After 30 minutes at -65°, 2.0 ml of triethyl 4-phosphonocrotonate is added dropwise. The reaction mixture is stirred for 30 minutes before a solution of 2.0 g of N-(3-pyridyl)indole-3-carboxaldehyde in 20 ml of tetrahydrofuran is slowly added while maintaining the temperature less than -60°. When the addition is complete, cooling is suspended and the reaction mixture slowly warms to room temperature at which temperature it is stirred for 4 hours. The solvent is evaporated and the residue is partitioned between 30 ml of methylene chloride and 20 ml of half saturated ammonium chloride solution. The organic phase is washed with 20 ml of water, dried over sodium sulfate and evaporated to give an oil which crystallizes from hot ethyl acetate to yield 3-[4-(ethoxycarbonyl)butadienyl]-N-(3-pyridyl)-indole, m.p. 112°-113°.

後処理

  1. additionis slowly added
  2. temperaturewhile maintaining the temperature less than -60°
  3. additionWhen the addition
  4. temperaturecooling
  5. customslowly warms to room temperature at which temperature it
  6. customThe solvent is evaporated
  7. customthe residue is partitioned between 30 ml of methylene chloride and 20 ml of half saturated ammonium chloride solution
  8. washThe organic phase is washed with 20 ml of water
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customto give an oil which
  12. customcrystallizes from hot ethyl acetate

出典と根拠

ORDレコード
ord-18411979e28c4fa1a9566c1f8071288c
出典データセット
uspto-grants-1985_08
特許番号
US04536505

反応ノート

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