Ethylene Oxide → 9-Methylfluorene-9-ethanol

HRID 2259278Notes

Reaction equation

HRID 2259278 reaction equation
[CH3:1][CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Li]CCCC.[CH2:20]1[O:22][CH2:21]1>C1COCC1>[CH3:1][C:2]1([CH2:20][CH2:21][OH:22])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 172999-MethylfluoreneHCID 178418339Butyllithium

Product 1

HCID 224070259-Methylfluorene-9-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 9-methylfluorene (10.0 g, 55.5 mmol) in 100 mL of THF was added n-BuLi (61.0 mmol) at -10° C., then a solution of ethylene oxide (61.0 mmol) in THF was added in one portion. The reaction mixture was stirred at -20° C., then allowed to warm to room temperature, quenched with NH4Cl solution and evaporated to a residue. This was then partitioned between ethyl acetate and water, the organic layer was washed with brine, dried with MgSO4 and evaporated to get the product which was purified by chromatography using 10% ethyl acetate/hexane mixture to provide a pure sample of 9-methylfluorene-9-ethanol, m.p. 84°-85° C.

Workup

  1. temperatureto warm to room temperature
  2. customquenched with NH4Cl solution
  3. customevaporated to a residue
  4. customThis was then partitioned between ethyl acetate and water
  5. washthe organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. customevaporated
  8. customto get the product which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-0a37ec2dd9ed4677a49ddb12b209c02d
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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