Method for preparing (E)-alpha-aryl-alpha,beta-unsaturated oxazoline or carboxylic acid and compound
An unsaturated and aryl group technology, applied in the field of organic chemical synthesis, to achieve mild reaction conditions, good selectivity and simple operation.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0034]
[0035] At -78°C, TMSOTf (181 μL, 1.0 mmol) was added to a solution of iodobenzene diacetate (161 mg, 0.5 mmol) in DCM (5 mL), and after stirring for 15 min, α, β- Unsaturated oxazoline compound (97.1 mg, 1.0 mmol). After stirring for 15 min, 4-picoline (93 mg, 1.0 mmol) was added. Then gradually raise the temperature to -10°C, continue the reaction for 24h and then add saturated NaHCO 3 The reaction was quenched with aqueous solution (5 mL), extracted with DCM (10 mL x 3). The organic phase was anhydrous Na 2 SO 4 Concentrated after drying, separated and purified by column chromatography (Rf=0.32, developing solvent: petroleum ether / ethyl acetate=2 / 1, v / v), the obtained product 2-(1-(2-iodophenyl)vinyl )-oxazoline is 106.2 mg of colorless oily liquid, and the yield is 71%.
[0036] 1 H NMR (600MHz, CDCl 3 ):δ7.86(dd,J=7.9,0.9Hz,1H),7.37–7.34(m,1H),7.31–7.26(m,1H),7.03–7.00(m,1H),6.27(s,1H ),5.61(s,1H),4.38(t,J=9.5Hz,2H),3.97(t,J=9.5Hz,2H).
[0037] 13 C N...
Embodiment 2
[0041]
[0042] At -78°C, TMSOTf (181 μL, 1.0 mmol) was added to a solution of iodobenzene diacetate (161 mg, 0.5 mmol) in DCM (5 mL), and after stirring for 15 min, α, β- Unsaturated oxazoline compound (111.1 mg, 1.0 mmol). After stirring for 15 min, 4-picoline (93 mg, 1.0 mmol) was added. Then gradually raise the temperature to -10°C, continue the reaction for 24h and then add saturated NaHCO 3 The reaction was quenched with aqueous solution (5 mL), extracted with DCM (10 mL x 3). The organic phase was anhydrous Na 2 SO 4 Concentrated after drying, separated and purified by column chromatography (Rf=0.37, developing solvent: petroleum ether / ethyl acetate=2 / 1, v / v), the obtained product (E)-2-(1-(2-iodobenzene yl)prop-1-en-1-yl)-oxazoline was 112.7 mg of colorless oily liquid, and the yield was 72%.
[0043] 1 H NMR (600MHz, CDCl 3 ): δ7.88(d, J=7.9Hz, 1H), 7.38–4.35(m, 1H), 7.17(dd, J=7.6, 1.5Hz, 1H), 7.03–6.98(m, 1H), 6.84( q,J=7.0Hz,1H), 4.38–4.26(m,2H),3.94–3.8...
Embodiment 3
[0049]
[0050] At -78°C, TMSOTf (181 μL, 1.0 mmol) was added to a solution of iodobenzene diacetate (161 mg, 0.5 mmol) in DCM (5 mL), and after stirring for 15 min, α, β- Unsaturated oxazoline compound (139.2 mg, 1.0 mmol). After stirring for 15 min, 4-picoline (93 mg, 1.0 mmol) was added. Then gradually raise the temperature to -10°C, continue the reaction for 24h and then add saturated NaHCO 3 The reaction was quenched with aqueous solution (5 mL), extracted with DCM (10 mL x 3). The organic phase was anhydrous Na 2 SO 4 Concentrated after drying, separated and purified by column chromatography (Rf=0.27, developing solvent: petroleum ether / ethyl acetate=2 / 1, v / v), the obtained product (E)-2-(1-(2-iodobenzene yl)pent-1-en-1-yl)-oxazoline was 117.7 mg of colorless oily liquid, and the yield was 69%.
[0051] 1 H NMR (600MHz, CDCl 3 ):δ7.87(dd,J=8.0,1.1Hz,1H),7.37–7.34(m,1H),7.16(dd,J=7.6,1.7Hz,1H),7.01–6.99(m,1H), 6.76(t,J=7.6Hz,1H),4.37–4.25(m,2H),3.93–3.89(m,2H),...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
