Ethyl Acetate → HCID 15045077, compound

HRID 1089859Notes

Reaction equation

HRID 1089859 reaction equation
[Li]CCCC.[CH3:6][C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.Br[CH2:21][CH2:22][CH:23]1[O:27][CH2:26][CH2:25][O:24]1.CCOC(C)=O>C1COCC1.CCCCCC>[CH3:6][C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]([CH2:21][CH2:22][CH:23]3[O:27][CH2:26][CH2:25][O:24]3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 152564-MethylfluoreneHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 15045077HCID 15045077, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of BuLi (2.5 M in hexane, 20.4 mL, 51.0 mmol) was slowly added into a cooled (-78° C.) solution of 4-methylfluorene (prepared according to Example 10; 9.0 g, 49.8 mmol) in 100 mL of THF. After 30 minutes 2-(2-bromoethyl)-1,3-dioxolane (18.9 g, 105.0 mmol) was added to the cold solution and the solution was warmed up to room temperature. The reaction mixture was stirred for weekend 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 11.2 g(82.8%) of the product.

Workup

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

Sources & evidence

ORD record
ord-dc8d0b8b968f47b092af3599e7cf89f8
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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