反应详情

温度

75 °C

A stirred solution of 6-iodoquinolin-3-ol (1.76 g, 6 mmol) in THF (10 mL) was treated with 2-tert-butoxy-2-oxoethylzinc chloride (39 ml, 19 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.6 mmol). After the addition, it was heated to reflux (75° C.) under N2. After 3 h, TLC 89368-3-1 showed no sign of starting material. Reaction was stop. The reaction was cooled to rt. Solvent was removed. The residue was stirred in EtOAc/10% EDTA (50 mL/50 mL) solution mixture. After 1 h, the organic layer was separated. The aqueous layer was extracted with more EtOAc (2×25 mL). The combined organic layers were washed with water, brine, dried over MgSO4, and removed solvent. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, hex:acetone=80%:20%, Flow=30 mL/min). to afford the desired product as brownish liquid. MS m/z: 260.3 (M+H). Calc'd. for C15H17NO3—259.2.

1. additionAfter the addition, it
2. temperaturewas heated
3. customReaction
4. temperatureThe reaction was cooled to rt
5. customSolvent was removed
6. waitAfter 1 h
7. customthe organic layer was separated
8. extractionThe aqueous layer was extracted with more EtOAc (2×25 mL)
9. washThe combined organic layers were washed with water, brine
10. dry with materialdried over MgSO4
11. customremoved solvent
12. customThe crude product was purified