反应详情

温度

0 °C

Add isopropyl magnesium chloride (2M solution in tetrahydrofuran, 2.98 mL, 5.95 mmol) to a solution of 1-(4-iodo-benzyloxy)-2-propyl-3-trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene (3.00 g, 5.41 mmol) in tetrahydrofuran (0.1M) cooled to 0° C. After 15 minutes, warm reaction to room temperature. After 1 hour, cool the reaction to −78° C. Add a solution of 2-formyl-isonicotinonitrile (612 mg, 5.95 mmol) in tetrahydrofuran (10 mL) via syringe. After 1 hour, warm the reaction to room temperature. Add 10% hydrochloric acid (30 mL). After 5 minutes, pour the reaction into water and extract with ethyl acetate. Combine organics, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with methanol:dichlormethane followed by trituration with acetonitrile to yield the title product as a white solid (1.71 g, 76%): 1H NMR (CDCl3) δ 0.95 (t, 3H), 1.56 (sextet, 2H), 2.56 (s, 3H), 2.69 (t, 2H), 4.50 (d, 1H), 5.16 (s, 2H), 5.84 (d, 1H), 6.46 (d, 1H), 7.41 (m, 4H), 7.51 (s, 1H), 7.55 (d, 1H), 8.76 (d, 1H), 12.74 (s, 1H).

1. temperaturewarm
2. customreaction to room temperature
3. waitAfter 1 hour
4. temperaturecool
5. customthe reaction to −78° C
6. waitAfter 1 hour
7. temperaturewarm
8. customthe reaction to room temperature
9. waitAfter 5 minutes
10. additionpour
11. extractionextract with ethyl acetate
12. dry with materialCombine organics, dry with sodium sulfate
13. filtrationfilter
14. concentrationconcentrate under reduced pressure
15. customto give a residue
16. customPurify the residue by flash chromatography
17. washeluting with methanol