Diethyl Ether → Fluorene-9-ethanol

HRID 2259270Notes

Reaction equation

HRID 2259270 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li]CCCC.CCCCCC.[CH2:25]1[O:27][CH2:26]1.CCOCC>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:25][CH2:26][OH:27])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6354Ethylene OxideHCID 6853FluoreneHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 10921761Fluorene-9-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(9-Fluorenyl)ethanol was prepared from a solution of fluorene (116.35 g, 0.7 mmol) in 800 ml of dry THF at -20° C. which was added n-BuLi in hexane (0.7 mol) keeping the temperature below -10° C. To the clear solution was rapidly added 357 ml of 1.4M ethylene oxide in ether (0.5 mol) keeping the temperature below 5° C. The reaction mixture was stirred for 5 hours, then quenched with 50 ml of saturated ammonium chloride solution. The THF was removed at a rotary evaporator. The residue was partitioned between water and ethyl acetate. The organic layer was separated, dried with MgSO4 and concentrated in vacuo until crystallization began. The solution was allowed to stand overnight and the crystals were collected and dried (mp 97° C.) (85.5 g, (81%)).

Workup

  1. customthe temperature below -10° C
  2. customthe temperature below 5° C
  3. customquenched with 50 ml of saturated ammonium chloride solution
  4. customThe THF was removed at a rotary evaporator
  5. customThe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo until crystallization
  9. waitto stand overnight
  10. customthe crystals were collected
  11. customdried (mp 97° C.) (85.5 g, (81%))

Sources & evidence

ORD record
ord-3c4a410720554a6b85759f3daec7ac6f
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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