Potassium Carbonate → 9-(2-Naphthyl)-10-triphenysilyl anthracene

HRID 270736ノート

反応式

HRID 270736 の反応式
Br[C:2]1[C:3]2[C:8]([C:9]([Si:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[C:2]1[C:15]2[C:10]([C:9]([Si:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:8]3[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:11][CH:12]=[CH:13][CH:14]=2

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 598339599-Bromo-l0-triphenysilyl anthracene

生成物 1

HCID 598339589-(2-Naphthyl)-10-triphenysilyl anthracene

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

9-bromo-10-triphenysilyl anthracene (4 g, 7.8 mmol), 2-naphthylboronic acid (1.6 g, 9.4 mmol) and K2CO3 (1.5 g,15.6 mmol) were dissolved in the solvent mixture of 50 mL ethylene glycol dimethyl ether and 75 mL water. The stirred solution was added tetrakis (triphenylphosphine) palladium (0) and the mixture refluxed under N2 for 16 hours. The reaction mixture was cooled and the water extracted with acetyl acetate three times. The combined organic phase was washed with portions of brine. The organic layer was then dried with MgSO4, filtered, and evaporated of solvent. The crude material was purified by column chromatography (n-hexane/acetyl acetate=10/1) to give 9-(2-naphthyl)-10-triphenysilyl anthracene (Compound 2), the reaction was following:

後処理

  1. temperaturethe mixture refluxed under N2 for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe water extracted with acetyl acetate three times
  4. washThe combined organic phase was washed with portions of brine
  5. dry with materialThe organic layer was then dried with MgSO4
  6. filtrationfiltered
  7. customevaporated of solvent
  8. customThe crude material was purified by column chromatography (n-hexane/acetyl acetate=10/1)

出典と根拠

ORDレコード
ord-593ab732c5ec421ba75b5e0d6f386ad3
出典データセット
uspto-grants-2008_11
特許番号
US07449593B2

反応ノート

読み込み中…