Hydrochloric Acid → 9,9-diethylfluorene
Reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([CH:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:7].BrCC.Cl>C1COCC1.O>[CH2:6]([C:8]1([CH2:1][CH3:2])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -75 °C
Procedure
A solution of n-butyllithium (77.34 cm3, 0.1934 mol, 2.5M in hexane) was added slowly to a solution of 9-ethylfluorene (25.00 g, 0.1289 mol) in THF (250 cm3) at −70° C. The solution was stirred for 1 hour at −75° C. and 1-bromoethane (17.59 cm3, 0.1934 mol) was added slowly. The solution was allowed to warm to room temperature and then stirred overnight. Dilute hydrochloric acid (200 cm3, 20%) was added to the reaction mixture and stirred for a further 10 minutes. Water (250 cm3) was added and the product extracted into diethyl ether (3×300 cm3). The combined organic extracts were dried (MgSO4) and the solvent removed on a rotary evaporator. The resulting oil was cooled to room temperature and recrystallised with ethanol to yield white crystals (19.50 g, 68%, m.pt. 60-62° C.).
Workup
- temperatureto warm to room temperature
- stirringstirred overnight
- stirringstirred for a further 10 minutes
- extractionthe product extracted into diethyl ether (3×300 cm3)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customthe solvent removed on a rotary evaporator
- temperatureThe resulting oil was cooled to room temperature
- customrecrystallised with ethanol
Sources & evidence
- ORD record
- ord-54bc1477c71f41b1a750d12ef7156177
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265163B2
Reaction notes
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