反应详情

1-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone (O2.071; 12.7 g) was dissolved in methanol/THF (200/200 ml) and admixed with phenyltrimethylammonium tribromide (13.1 g) while stirring. The mixture was stirred at RT for 1 h, then diluted with DCM and washed once with 5% sodium thiosulfate solution. The DCM phase was dried over magnesium sulfate, filtered and concentrated. The residue was taken up in acetonitrile (100 ml) and admixed with 48% hydrobromic acid (5.91 ml). The mixture was left to stand for 1 h, then admixed with water, extracted by shaking with EA, and the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min). 3.29 g of the title compound were obtained.

1. stirringThe mixture was stirred at RT for 1 h
2. washwashed once with 5% sodium thiosulfate solution
3. dry with materialThe DCM phase was dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. waitThe mixture was left
7. extractionextracted
8. stirringby shaking with EA
9. dry with materialthe combined EA phases were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified
13. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min)