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 3 x with ethyl acetate. The combined extracts were washed 1 x 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 3 x with ethyl acetate
- washThe combined extracts were washed 1 x 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-9897c614ae764c99ace1cce82d34d448
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04970229
Reaction notes
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