반응 #706806
ord-82c06b0e6b584a33b9b008781e089000
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후처리
- 1기타to give a yellow solution
- 2온도This solution was heated to 50° C. for 2 hours
- 3온도cooled to room temperature
- 4기타the reaction quenched by the addition of saturated aqueous NH4Cl
- 5추출The solution was extracted with EtOAc
- 6세척the combined organic layers were washed with H2O and saturated aqueous NaCl
- 7건조before being dried (MgSO4)
- 8농축concentrated under reduced pressure
실험 절차
A solution of 4-tert-butylbromobenzene (149.0 mg, 0.70 mmol) in 2.0 mL of THF was cooled to -78° C. and tert-butyllithium (92.6 mg, 1.44 mmol, 0.85 ml of a 1.7M solution in pentane) was added to give a yellow solution. After 30 minutes a solution of ZnCl2 (133.0 mg, 0.98 mmol) in 4.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature and transferred via cannula to a solution of ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thiochromen-6-ylethynyl) benzoate (Compound 224, 140.0 mg, 0.28 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.0 mg, 0.02 mmol) in 2.0 mL THF. This solution was heated to 50° C. for 2 hours, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. The solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 94.0 mg (70%), was isolated by column chromatography (5% EtOAc/hexanes) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ: 7.98 (2H, d, J=8.3 Hz), 7.52 (2H, d, J=8.3 Hz), 7.43-7.22 (7H, m), 5.86 (1H, s), 4.38 (2H, q, J=7.1 Hz), 1.47 (6H, s), 1.40 (3H, t, J=7.1 Hz), 1.38 (9H, s).