Ethyl Acetate → 4-Ethoxycarbonyl-5-ethynylthiazole
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1I)=[O:5])[CH3:2].[CH2:12]([Sn](CCCC)(CCCC)C#C)[CH2:13]CC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(OCC)(=O)C>CN1CCCC1=O.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[C:12]#[CH:13])=[O:5])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
4-Ethoxycarbonyl-5-iodothiazole (1.45 g) was dissolved in 25 ml of N-methyl-2-pyrrolidinone. Tri-n-butylethynyltin (1.78 ml), 143 mg of tri(2-furyl)phosphine, 143 mg of tris(dibenzylideneacetone)dipalladium(0), and 1.43 g of zinc chloride were added to the solution under an argon atmosphere, and the mixture was stirred at room temperature for 40 min. Brine and ethyl acetate were added to the reaction solution. The insolubles were removed by filtration through Celite, and the filtrate was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give 750 mg of the title compound.
Workup
- customThe insolubles were removed by filtration through Celite
- extractionthe filtrate was extracted twice with ethyl acetate
- washwere washed with brine
- dry with materialwere dried over anhydrous magnesium sulfate
- filtrationwere filtered
- concentrationwere concentrated under the reduced pressure
- customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-91ca0aee4829420f884d7344a9da5883
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344154B2
Reaction notes
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