Ethyl Acetate → 2-[(2-Methoxyfluoren-9-yl)ethyl]-1,3-dioxolane

HRID 1089856Notes

Reaction equation

HRID 1089856 reaction equation
[Li]CCCC.[CH3:6][O:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1.Br[CH2:22][CH2:23][CH:24]1[O:28][CH2:27][CH2:26][O:25]1.CCOC(C)=O>C1COCC1.CCCCCC>[CH3:6][O:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([CH2:22][CH2:23][CH:24]3[O:28][CH2:27][CH2:26][O:25]3)[C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 173012-MethoxyfluoreneHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 538664562-[(2-Methoxyfluoren-9-yl)ethyl]-1,3-dioxolaneYield 68.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of n-BuLi (2.5 M in hexane, 6.4 mL, 16.0 mmol) was slowly added into a cooled (-78° C.) solution of 2-methoxyfluorene (prepared according to example 10; 3.1 g, 15.8 mmol) in 100 ml THF. The reaction mixture became dark red and a solid started to precipitate out. After 30 minutes 2-(2-bromoethyl)-1,3-dioxolane (5.8 g, 32.0 mmol) was added to the cold solution and the solution was warmed up to room temperature. The reaction mixture was stirred overnight at room temperature. TLC (silica, 25% EtOAc in hexane) was used to monitor the reaction. The reaction was quenched with water and the product was extracted into EtOAc. The organic layer was washed with water (×3), dried over magnesium sulfate and evaporated. Short path chromatography (5% ethyl acetate/hexane) afforded 3.2 g (62.5%) of the product.

Workup

  1. customto precipitate out
  2. customthe reaction
  3. customThe reaction was quenched with water
  4. extractionthe product was extracted into EtOAc
  5. washThe organic layer was washed with water (×3)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-e88bbb653ace4aaea305f0e3d8cb53ff
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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