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

HRID 37024
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HRID 37024 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-620e0f6b5c9442309cbc7141c28d9b96
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05419851

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