Butylamine → (E)-3,4-difluoro-1-(4-propylphenyl)-4-[4-(2-p-toluylethynyl)phenyl]-3-buten-1-yne

HRID 37024

反応式

HRID 37024 の反応式
[F:1]/[C:2](=[C:14](/[F:22])\[C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)/[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1.C(N)CCC.[C:28]1([CH3:36])[CH:33]=[CH:32][C:31]([C:34]#[CH:35])=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[F:1]/[C:2](=[C:14](/[F:22])\[C:15]1[CH:20]=[CH:19][C:18]([C:35]#[C:34][C:31]2[CH:32]=[CH:33][C:28]([CH3:36])=[CH:29][CH:30]=2)=[CH:17][CH:16]=1)/[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 8007ButylamineHCID 13018p-EthynyltolueneHCID 516892Sodium BicarbonateHCID 86748683(E)-3,4-difluoro-1-(4-propylphenyl)-4-(4-bromophenyl)-3-buten-1-yne

生成物 1

HCID 86748682(E)-3,4-difluoro-1-(4-propylphenyl)-4-[4-(2-p-toluylethynyl)phenyl]-3-buten-1-yne収率 65%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Into a 100 ml three-necked flask, 2.86 g of cuprous iodide, 4.33 g (0.012 mol) of (E)-3,4-difluoro-1-(4-propylphenyl)-4-(4-bromophenyl)-3-buten-1-yne obtained in Example 4 and 30 ml of dry THF were charged under an argon atmosphere, followed by stirring at room temperature. Then, 1.42 g of n-butylamine and 1.53 g of p-toluylacetylene were added thereto. Then, 10 ml of a dry THF solution containing 0.69 g of (Ph3P)4Pd was added thereto, and the mixture was stirred at room temperature for 2 hours. After an addition of 30 ml of a saturated NaHCO3 aqueous solution, the mixture was subjected to liquid separation, and then extracted with methylene chloride. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 3.09 g (yield: 65%) of (E)-3,4-difluoro-1-(4-propylphenyl)-4-[4-(2-p-toluylethynyl)phenyl]-3-buten-1-yne.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customthe mixture was subjected to liquid separation
  4. extractionextracted with methylene chloride
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-620e0f6b5c9442309cbc7141c28d9b96
出典データセット
uspto-grants-1995_05
特許番号
US05419851

関連ノート

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