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Fluorene → HCID 15045041, 화합물

HRID 440343
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HRID 440343 반응식
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1.CCCCCC.C(OCC)(=O)C>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:20][CH2:21][CH:22]3[O:26][CH2:25][CH2:24][O:23]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
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6

반응물 4

HCID 6853FluoreneHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

생성물 1

HCID 15045041HCID 15045041, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

2-(9-Fluorenyl)ethyl-1,3-dioxolane was prepared from a solution of fluorene (30.0 g, 180.5 mmol) in 400 ml of dry THF cooled in a -78° C. bath under argon, to which was added 100 ml of n-butyllithium (2.0M in cyclohexane) over 15 minutes After stirring for 0.5 hours at 78° C. 2-(2-bromoethyl)-1, 3-dioxolane (22.3 ml, 190 mmol) was added dropwise, and the resulting solution stirred at room temperature for 16 hours. Concentration in vacuo yielded an orange residue which was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was then washed with brine, dried with magnesium sulfate, and concentrated in vacuo to afford an orange oil. Flash chromatography on silica, hexane:ethyl acetate 20:1 to 1:1 yielded a yellow oil (36.38 g, 76%).

후처리

  1. stirringthe resulting solution stirred at room temperature for 16 hours
  2. concentrationConcentration in vacuo
  3. customyielded an orange residue which
  4. customwas partitioned between ethyl acetate and saturated ammonium chloride
  5. washThe organic layer was then washed with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford an orange oil

출처 및 근거

ORD 기록
ord-368a5c9bc3f34386b6f90389a02404a4
출처 데이터셋
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05519043

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