Water → 4-hydroxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one
Reaction equation
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[CH:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]#[N:24])[CH:18]=[CH:19][CH:20]=1)=O.N1CCCCC1.O>C(Cl)(Cl)Cl>[OH:10][C:9]1[CH:8]=[C:7]([CH3:11])[O:6][C:5](=[O:12])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:13][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:22][C:23]#[N:24])[CH:16]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5.24 g of 3-acetyl-4-hydroxy-6-methyl-2H -pyran-2-one, 4.90 g of 3-(3-formylphenyl)-2-propenenitrile and 1.92 g of piperidine in 40 ml of chloroform was heated under refluxing for 35 minutes while water was removed with a Soxhlet's extractor filled with a molecular sieve. After cooling to room temperature, the reaction mixture washed successively with 10% hydrochloric acid, and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. Precipitated crystals were filtered, and the crystals were subjected to silica gel column chromatography to obtain 4.05 g of 4-hydroxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (1a)] as a pale yellow crystal.
Workup
- customwas removed with a Soxhlet's extractor
- additionfilled with a molecular sieve
- washthe reaction mixture washed successively with 10% hydrochloric acid
- dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customPrecipitated crystals
- filtrationwere filtered
Sources & evidence
- ORD record
- ord-d31473112fad496b9835a7d015f7a86d
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691883B2
Reaction notes
Loading…