2-[4-(Propan-2-yl)phenyl]prop-2-enal → 3-[4-(1-Methylethyl)phenyl]-3-buten-2-ol
Reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH2:13])[CH:11]=[O:12])=[CH:6][CH:5]=1)[CH3:3].[CH3:14][Li]>C(OCC)C>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[CH2:13])[CH:11]([OH:12])[CH3:14])=[CH:8][CH:9]=1)[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
6.1 g of aldehyde 44 is dissolved in 250 ml of diethyl ether and cooled under nitrogen to −78° C. 35.8 ml of a methllithium solution (1.6 M in diethyl ether) is now added in drops. After 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby 2.8 g of title compound 45 accumulates as a colorless oil.
Workup
- customAfter 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution
- extractionextracted with ethyl acetate
- washwashed with sodium chloride solution
- customdried on sodium sulfate
- customthe solvent is removed
- customThe residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby 2.8 g of title compound 45 accumulates as a colorless oil
Sources & evidence
- ORD record
- ord-1f1c838c65b54d7f90c80bc3b4f4810d
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613920B1
Reaction notes
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