Butyllithium → 7-(alpha-Hydroxybutyl)-4-isopropyl-2-hydroxy-2,4,6-cycloheptatrien-1-one
Reaction equation
[CH:1]([C:3]1[C:9](=[O:10])[C:8]([OH:11])=[CH:7][C:6]([CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1)=[O:2].[CH2:15]([Li])[CH2:16][CH2:17]C>O1CCCC1.CCCCCC>[OH:2][CH:1]([C:3]1[C:9](=[O:10])[C:8]([OH:11])=[CH:7][C:6]([CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1)[CH2:15][CH2:16][CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
7-formyl-4-isopropyl-2-hydroxy-2,4,6-cycloheptatrien-1-one (1.95 g, 10 mmol) was dissolved in tetrahydrofuran (30 ml) and the resultant was cooled to -78° C. in a dry ice/acetone bath. A solution of n-butyllithium in hexane (1.6M, 14 ml) was added dropwise to the solution, then, the dry ice/acetone bath was removed and the resultant was stirred until insoluble matter was dissolved. An aqueous saturated ammonium chloride was added to the reaction mixture and the resultant was extracted with methylene chloride. The methylene chloride layer was washed with water, then dried over anhydrous sodium sulfate. Solvent was distilled off to give 2.72 g of 7-(α-hydroxybutyl)-4-isopropyl-2-hydroxy-2,4,6-cycloheptatrien-1-one as a reddish brown oil (yield: quantitative).
Workup
- customthe dry ice/acetone bath was removed
- dissolutionwas dissolved
- additionAn aqueous saturated ammonium chloride was added to the reaction mixture
- extractionthe resultant was extracted with methylene chloride
- washThe methylene chloride layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationSolvent was distilled off
Sources & evidence
- ORD record
- ord-d43cdc1c509b4abc889cdf6098cf5ca9
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05703071
Reaction notes
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