1-Methylfluorene → HCID 15045094, compound

HRID 1089852Notes

Reaction equation

HRID 1089852 reaction equation
[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Li][CH2:16][CH2:17][CH2:18]C.BrC1[O:25][CH2:24][CH2:23][O:22]1.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:18][CH2:17][CH:16]3[O:25][CH2:24][CH2:23][O:22]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 156041-MethylfluoreneHCID 143725662-Bromo-1,3-dioxolaneHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Product 1

HCID 15045094HCID 15045094, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-Methylfluorene (3.2 g, 18.0 mmol) in 50 mL THF was charged with BuLi, 2.35M solution in hexanes (7.65 mL, 18.0 mmol) at -78° C. The reaction mixture was stirred for 2 hr at -78° C. then 2-bromo-1.3-dioxolane (3.6 g, 19.8 mmol) was added by a syringe. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The reaction mixture was stirred for 2 hr at room temperature then the THF was evaporated. The residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate, treated with a coarse silica gel and Norit and evaporated to yield 4.8 g (96.6%) of the desired product.

Workup

  1. stirringThe reaction mixture was stirred for 2 hr at room temperature
  2. customthe THF was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with a coarse silica gel and Norit
  7. customevaporated

Sources & evidence

ORD record
ord-6835f0d10da447f0909bd007befd7676
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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