Ethylene Oxide → Fluorene-9-ethanol
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.[CH2:19]1[O:21][CH2:20]1>C1COCC1.CCOCC>[CH:1]1[C:13]2[CH:12]([CH2:19][CH2:20][OH:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred, cooled (-78° C.) solution of 6.00 g (36.1 mmol) of fluorene in 75 mL of THF was added 15.4 mL (36.2 mmol) of 2.35 M n-BuLi in hexanes dropwise. The resulting dark orange mixture was stirred for 1.5 h and 26.0 mL (36.4 mmol) of 1.4 M ethylene oxide in Et2O was added. The resulting bright orange mixture was warmed slowly to room temperature over 3.5 h, quenched with saturated aqueous NH4Cl and concentrated at reduced pressure. The residue was poured into water and extracted twice with Et2O. The combined organic layers were washed with brine and dried over magnesium sulfate. Solvent was removed at reduced pressure and the crude product was chromatographed on 150 g of flash silica gel eluting with 25% EtOAc in hexane to afford 5.05 g (67%) of the desired alcohol as a white solid, mp 98°-99° C.
Workup
- customquenched with saturated aqueous NH4Cl
- concentrationconcentrated at reduced pressure
- additionThe residue was poured into water
- extractionextracted twice with Et2O
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- customSolvent was removed at reduced pressure
- customthe crude product was chromatographed on 150 g of flash silica gel eluting with 25% EtOAc in hexane
Sources & evidence
- ORD record
- ord-3060891a4fa14969b3fb6a0ecdbe5369
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05079260
Reaction notes
Loading…