Fluorene → HCID 67259085、化合物

HRID 2425314ノート

反応式

HRID 2425314 の反応式
[Li]CCCC.[CH:6]1[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.Cl[Si:20]([CH:23]1[C:31]2[C:26](=[C:27]([CH3:33])[CH:28]=[C:29]([CH3:32])[CH:30]=2)[CH:25]=[C:24]1[CH3:34])([CH3:22])[CH3:21].[Li]>CCCCCC.CCOCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:34][C:24]1[CH:23]([Si:20]([CH:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[C:18]2=[CH:6][CH:7]=[CH:8][CH:9]=3)([CH3:22])[CH3:21])[C:31]2[C:26]([CH:25]=1)=[C:27]([CH3:33])[CH:28]=[C:29]([CH3:32])[CH:30]=2

参加物

9

反応物 4

HCID 6853FluoreneHCID 3028194LithiumHCID 59735669HCID 59735669、化合物HCID 178418339Butyllithium

生成物 1

HCID 67259085HCID 67259085、化合物収率 99.3%

試薬・触媒・溶媒 4

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A 2.5 M n-BuLi solution in hexane (9.6 mL) was added dropwise at 0° C. under stirring to a solution of 3.78 g of fluorene in 40 ml of Et2O in a 100 mL Schlenk flask. After 30 min the resulting orange solution was allowed to warm up to room temperature and stirred for 3 days. A solution of chloro(2,4,6-trimethylindenyl)dimethylsilane (22.60 mmol) in 20 mL of THF was cooled to 0° C. and slowly added to the lithium salt solution, also previously cooled to 0° C. At the end of the addition a light brown suspension was obtained. The latter was allowed to warm up to room temperature and stirred for 24 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 50 mL of toluene and then filtered to remove LiCl. The filtrate was dried in vacuo to give 8.54 g of a brown oil. The product was characterized by 1H-NMR spectroscopy: there are the signals of two isomeric species: allylic and vinylic (2:1). The product was used as such in the next step without further purification.

後処理

  1. temperaturealso previously cooled to 0° C
  2. additionAt the end of the addition a light brown suspension
  3. customwas obtained
  4. temperatureto warm up to room temperature
  5. stirringstirred for 24 h
  6. customThen the reaction mixture was evaporated under reduced pressure
  7. customto give a brown sticky solid, which
  8. filtrationfiltered
  9. customto remove LiCl
  10. customThe filtrate was dried in vacuo

出典と根拠

ORDレコード
ord-c7c459e8ec3f4c96844012512b83419a
出典データセット
uspto-grants-2011_06
特許番号
US07964679B2

反応ノート

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