Fluorene → HCID 67259085、化合物

HRID 2425307ノート

反応式

HRID 2425307 の反応式
[Li]CCCC.CCCCCC.[CH:12]1[C:24]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.Cl[Si:26]([CH:29]1[C:37]2[C:32](=[C:33]([CH3:39])[CH:34]=[C:35]([CH3:38])[CH:36]=2)[CH:31]=[C:30]1[CH3:40])([CH3:28])[CH3:27].[Li]>CCOCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:40][C:30]1[CH:29]([Si:26]([CH:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:24]2=[CH:12][CH:13]=[CH:14][CH:15]=3)([CH3:28])[CH3:27])[C:37]2[C:32]([CH:31]=1)=[C:33]([CH3:39])[CH:34]=[C:35]([CH3:38])[CH:36]=2

参加物

9

反応物 5

HCID 6853FluoreneHCID 8058HexaneHCID 3028194LithiumHCID 59735669HCID 59735669、化合物HCID 178418339Butyllithium

生成物 1

HCID 67259085HCID 67259085、化合物収率 108.2%

試薬・触媒・溶媒 3

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

実験手順

A 2.5 M n-BuLi solution in hexane (16.75 mL, 41.88 mmol) was added dropwise at 0° C. under stirring to a solution of 6.63 g of fluorene (39.89 mmol) in 100 ml of Et2O in a 500 mL 3-necked round flask. The resulting orange solution was allowed to warm up to room temperature and stirred for 1.5 h. A solution of chloro(2,4,6-trimethyl-indenyl)dimethylsilane (10 g, 39.87 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 1.5 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 150 mL of toluene and then filtered to remove LiCl. The filtrate was dried in vacuo to give 16.42 g of a brown oil, which resulted to be the expected ligand contaminated by minor amounts of non identified by-products (crude yield quantitative). 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 1.5 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-da257939f86b4d82ac9927cc3327c4c6
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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