反应详情

温度

100 °C

To a stirring suspension of 4-(thiazol-2-yl)benzaldehyde (349 mg, 1.84 mmol), tricyclohexylphosphine (27 mg, 0.07 mmol), pivalic acid (64.2 μl, 0.55 mmol), potassium carbonate (382 mg, 2.77 mmol) and palladium (II) acetate (8 mg, 0.04 mmol) in DMA (5.15 mL) under nitrogen was added a solution of 1-bromo-4-(heptyloxy)benzene (500 mg, 1.84 mmol) in DMA (1 mL). The reaction mixture was evacuated and purged with nitrogen 3 times then heated at 100° C. for 6 h. Once cooled, the reaction mixture was diluted with EA (40 mL), washed with water (3×40 mL) and brine (40 mL). The organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford a brown-green solid. The crude product was purified by chromatography (0-50% EA in hexanes) to afford 270 mg (37%) of 4-(5-(4-(heptyloxy)phenyl)thiazol-2-yl)benzaldehyde as an iridescent yellow solid. LCMS-ESI (m/z) calculated for C23H25NO2S: 379.5. found 380.0 [M+H]+, tR=2.99 min. (Method 8).

1. customThe reaction mixture was evacuated
2. custompurged with nitrogen 3 times
3. temperatureOnce cooled
4. additionthe reaction mixture was diluted with EA (40 mL)
5. washwashed with water (3×40 mL) and brine (40 mL)
6. dry with materialThe organic phase was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto afford a brown-green solid
10. customThe crude product was purified by chromatography (0-50% EA in hexanes)