Diisopropylamine → Lithium diisopropylamide

HRID 931694

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HRID 931694 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:14]2[C:10](=[N:11][S:12][N:13]=2)[C:9]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][CH:7]=1.[CH:20]([NH:23][CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21].[Li:27]CCCC.[CH3:32][Sn:33](Cl)([CH3:35])[CH3:34]>C1COCC1>[Li+:27].[CH3:21][CH:20]([N-:23][CH:24]([CH3:26])[CH3:25])[CH3:22].[CH3:32][Sn:33]([CH3:35])([CH3:34])[C:17]1[S:16][C:15]([C:9]2[C:10]3[C:14](=[N:13][S:12][N:11]=3)[C:6]([C:2]3[S:1][C:5]([Sn:33]([CH3:35])([CH3:34])[CH3:32])=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 14016Trimethyltin chlorideHCID 3962944,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazoleHCID 178418339Butyllithium

생성물 2

HCID 2724682Lithium diisopropylamideHCID 581530092,1,3-Benzothiadiazole, 4,7-bis(5-(trimethylstannyl)-2-thienyl)-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Compound (1) was dissolved in anhydrous THF (20 ml) in a nitrogen-filled flask. The solution was cooled down to −78° C. LDA was prepared from the reaction of diisopropylamine (0.5 g, 5.1 mmol, 3 eq.) and n-BuLi (3.12 ml, 5.1 mmol, 3 eq.) (1.6 M hexane solution) in anhydrous THF (2 ml), which was added to the above solution dropwise. After stirring for 1 h, trimethylstannyl chloride (3.8 ml, 3.8 mmol, 2.3 eq.) (1 M THF solution) was added and reacted for 1 h. The reaction was quenched by addition of water and the organic layer was extracted with ether, washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, the residue was purified by recrystallization from ethanol, giving the title compound as a needle-shaped purple crystal.

후처리

  1. additionfilled flask
  2. additionwas added to the above solution dropwise
  3. customreacted for 1 h
  4. customThe reaction was quenched by addition of water
  5. extractionthe organic layer was extracted with ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the solvent was removed under reduced pressure
  9. customthe residue was purified by recrystallization from ethanol

출처 및 근거

ORD 기록
ord-4d36d403e34f4f5eb6ff3d944dfca4b1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296864B2

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