Fluorene → HCID 22146523, compound

HRID 1957761Notes

Reaction equation

HRID 1957761 reaction equation
[CH2:1]([Si:9]([CH3:12])(Cl)Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:13]1[C:25]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:1]([Si:9]([CH3:12])([CH:24]1[C:25]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:25]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 6853Fluorene2×HCID 84649Dichloro(methyl)octylsilane

Product 1

HCID 22146523HCID 22146523, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Octylmethyldichlorosilane (32.68 g, 0.144 mol) and 200 mL of dry THF were charged to a one liter Schlenk flask equipped with an addition funnel. Fluorene anion (49.50 g, 0.288 mol) was dissolved in approximately 200 mL of dry THF and charged to the addition funnel. The temperature of the stirring solution was lowered to -20° C. under positive nitrogen pressure. The fluorene anion was added dropwise over two hours. After the addition of anion was complete the reaction mixture was allowed to warm to room temperature. The solution was then stirred overnight. The solution was washed with three 200 mL aliquots of water, retaining the organic layer after each washing. The organic layer was dried with magnesium sulfate and filtered. The product was recrystallized from a diethyl ether/methanol solution. The yield of this reaction is 10%.

Workup

  1. customequipped with an addition funnel
  2. additioncharged to the addition funnel
  3. customwas lowered to -20° C. under positive nitrogen
  4. additionAfter the addition of anion
  5. washThe solution was washed with three 200 mL aliquots of water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. customThe product was recrystallized from a diethyl ether/methanol solution

Sources & evidence

ORD record
ord-8f2de968ffce468191d40c4bd571b81e
Source dataset
uspto-grants-1998_07
Patent number
US05786495

Reaction notes

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