Fluorene → HCID 67259085, 화합물

HRID 2425314노트

반응식

HRID 2425314 반응식
[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

참가 물질

9

반응물 4

HCID 6853FluoreneHCID 3028194LithiumHCID 59735669HCID 59735669, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67259085HCID 67259085, 화합물수율 99.3%

시약·촉매·용매 4

HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7c459e8ec3f4c96844012512b83419a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964679B2

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