Dichlorodimethylsilane → Chlorodimethyl(n-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indol-6-yl)silane

HRID 1581731ノート

反応式

HRID 1581731 の反応式
[Li]CCCC.CCCCCC.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=2)[C:15]2[C:23]3[C:28]([CH2:29][C:14]1=2)=[CH:27][CH:26]=[CH:25][CH:24]=3.N1C2C(C=CC3C=2C=C2C=3C=CC=C2)=CC=1.[Cl:46][Si:47](Cl)([CH3:49])[CH3:48]>C1COCC1>[Cl:46][Si:47]([CH3:49])([CH3:48])[CH:29]1[C:14]2[N:13]([CH3:12])[C:21]3[C:16]([C:15]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=3

参加物

7

反応物 5

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 155337292,5-Dimethyl-5,6-dihydroindeno[2,1-b]indoleHCID 178418339Butyllithium2 回HCID 178420856HCID 178420856、化合物

生成物 1

HCID 22722355Chlorodimethyl(n-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indol-6-yl)silane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

9.5 mL of a 2.5 M solution of n-BuLi in hexane (23.75 mmol) were added dropwise to a solution of 5.1 g of N-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indole, obtained as reported above, (purity 98.2%, Mw=233.32, 21.46 mmol; indenoindole: n-BuLi=1:1.1) in 70 mL of THF, previously cooled to −78° C. At the end of the addition, the brown solution was allowed to warm up to room temperature and stirred for 6 hours. Then it was cooled again to −78° C. and added dropwise to a solution of dichlorodimethylsilane (Mw=129.06, d=1.064, 2.6 mL, 21.43 mmol; indenoindole: Me2SiCl2=1:1) in 20 mL of THF, previously cooled to −78° C. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred overnight. The solvents were evaporated under reduced pressure to give a brown sticky solid, which at the 1H-NMR analysis resulted to be the target product, with few by-products. The product was used in the subsequent step without further purification.

後処理

  1. customobtained
  2. additionAt the end of the addition
  3. temperatureto warm up to room temperature
  4. temperatureThen it was cooled again to −78° C.
  5. temperaturepreviously cooled to −78° C
  6. additionAt the end of the addition
  7. temperatureto warm up to room temperature
  8. stirringstirred overnight
  9. customThe solvents were evaporated under reduced pressure
  10. customto give a brown sticky solid, which at the 1H-NMR analysis
  11. customresulted
  12. customThe product was used in the subsequent step without further purification

出典と根拠

ORDレコード
ord-b028dc6e860d4855b92625b7b613b900
出典データセット
uspto-grants-2004_05
特許番号
US06730754B2

反応ノート

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