反应详情

A mixture of 2-(thiazol-2-yloxy)ethanol (6.39 g, 44.0 mmol), 2,6-dichloro-p-cresol (15.6 g, 88.0 mmol), azodicarboxylic-dipiperidide (22.2 g, 88.0 mmol) and PBu3 (85%, 38.3 mL, 132 mmol) in toluene (325 mL) was heated to reflux for 30 min. The mixture was allowed to cool to rt, filtered, and the precipitate was washed thoroughly with toluene. The filtrate was evaporated under reduced pressure. The residue was diluted with EtOAc, and washed with aq. 1M NaOH (4×). The org. phase was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:19→1:9→1:4) yielded the title compound as a colourless solid (9.24 g, 69%). LC-MS: tR=1.06 min, ES+: 304.05.

1. temperaturewas heated
2. temperatureto reflux for 30 min
3. filtrationfiltered
4. washthe precipitate was washed thoroughly with toluene
5. customThe filtrate was evaporated under reduced pressure
6. additionThe residue was diluted with EtOAc
7. washwashed with aq. 1M NaOH (4×)
8. dry with materialphase was dried over MgSO4
9. filtrationfiltered
10. customthe solvents were removed under reduced pressure
11. customPurification of the crude by FC (EtOAc/heptane 1:19→1:9→1:4)