Diethylamine → HCID 15087631, compound
Reaction equation
C(NCC)C.[C:6]([OH:12])(=[O:11])[CH2:7][CH2:8][C:9]#[CH:10].[I:13][C:14]1[S:15][CH:16]=[C:17](I)[CH:18]=1>>[I:13][C:14]1[S:15][C:16]([C:10]#[C:9][CH2:8][CH2:7][C:6]([OH:12])=[O:11])=[CH:17][CH:18]=1Participants
Procedure
To 75 ml of diethylamine was added with stirring 3.76 g of 4-pentynoic acid, 22 g of 2.4-diiodothiophene, and 300 mg of tetrakis-(triphenylphosphine)palladium(o). The slurry was degassed with argon and 960 mg of CuI was added. The slurry was maintained under argon and allowed to stir overnight, producing a dark brown solution. Thereafter, the solvent was removed under reduced pressure and 100 ml of 10% HCl was added to the residue. The residue was filtered and then extracted 3x with ethyl acetate. The combined extracts were washed lx with water, dried over anhydrous MgSO4, filtered and stripped. The resulting residue was flash chromatographed on a column of silica gel. Elution with a mixture of 30/70/2 parts ethyl acetate/hexane/acetic acid produced 3.5 g of the titled product as a yellow solid.
Workup
- customThe slurry was degassed with argon and 960 mg of CuI
- additionwas added
- temperatureThe slurry was maintained under argon
- customproducing a dark brown solution
- customThereafter, the solvent was removed under reduced pressure and 100 ml of 10% HCl
- additionwas added to the residue
- filtrationThe residue was filtered
- extractionextracted 3x with ethyl acetate
- washThe combined extracts were washed lx with water
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customchromatographed on a column of silica gel
- washElution
- additionwith a mixture of 30/70/2 parts ethyl acetate/hexane/acetic acid
Sources & evidence
- ORD record
- ord-efcfb6de8e7242efb1224aeac8b081df
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04970234
Reaction notes
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