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With sodium hydride; In tetrahydrofuran; mineral oil; at 100.0℃; for 8.0h;
5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 2-Methoxy-benzoic acid phenyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Methoxy-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.53 g, 8.3 mmol) as yellow solid in 59% yield.
59%
With sodium hydride; In tetrahydrofuran; mineral oil; at 100.0℃; for 8.0h;
5,6-dihydro-cyclopenta [b] thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60%, 1.5 g, 36 mmol).To the addition of 2-methoxy-benzeneAcid phenyl ester,The reaction mixture was heated to 100 & lt; 0 & gt; C and maintained for 8 hours. The solution was cooled to room temperature and poured into water. The product mixture was acidified with concentrated hydrochloric acid and ethyl acetate (70 mL) was added. The organic layer was collected, treated with brine, dried over MgSO4 (s) and concentrated under reduced pressure. The resulting precipitate was collected and recrystallized from ethanol to give the corresponding 5- (2-methoxy-benzoyl) -5,6-dihydro-cyclopenta [b] thiophen-4-one (2.53 G, 8.3 mmol) as a yellow solid in 59% yield
With 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); nickel(II) acetate tetrahydrate; sodium carbonate; In 1,4-dioxane; at 160℃; for 24h;Inert atmosphere;
General procedure: A 20-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar,Ni(OAc)2·4H2O (10.0 mg, 0.040 mmol, 10 mol%) and Na2CO3 (63.6 mg, 0.60 mmol, 1.5 equiv) weredried with a heatgun in vacuo and filled with N2 gas after cooling to room temperature. To this wereadded aromatic ester 1 (0.40 mmol, 1.0 equiv), 2-morpholinoacetonitrile (2a: 100.9 mg, 0.80 mmol,2.0 equiv) and dcypt (38.1 mg, 0.080 mmol, 20 mol%). The vessel was placed under vacuum andrefilled N2 gas three times, and then added 1,4-dioxane (1.6 mL). The vessel was sealed with O-ringtap and then heated at 150-160 C for 12 hours in an oil bath or 9-well reaction block with stirring.After cooling the reaction mixture to room temperature, the mixture was passed through a shortsilica-gel pad with EtOAc as an eluent. The filtrate was concentrated in vacuo. The residue waspurified by Isolera or PTLC to afford the corresponding aryl nitrile 3.
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