反应详情

To a solution of 4-(2-tetrahydropyran-2-yloxyethyl)phenol (9, 8.0 g, 36 mmoles) in 2-butanone (100 mL) were added K2CO3 (10.0 g, 72 mmoles) and 3-bromopropanol (6.5 mL, 72 mmoles). The solution was refluxed 18 hours with mechanical stirring. After cooling, the mixture was filtered and the solvent removed under reduced pressure to afford 13.0 g of crude oil. This was purified by flash chromatography on silica gel (solvent=80:20 ethyl acetate:heptane). The pure fractions were pooled and the solvent removed in vacuo to give 7.0 g of 1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(3-hydroxypropy)benzene (10). NMR (CDCl3)δppm: 7.0(q, 4H); 4.58(s, 1H)' 4.3-3.3(m, 8H); 3.06(s, 1H); 2.83(t, 2H); 1.83(m, 2H); 1.63(m, 6H). (Scheme II, Step 5.)

1. temperatureThe solution was refluxed 18 hours with mechanical stirring
2. temperatureAfter cooling
3. filtrationthe mixture was filtered
4. customthe solvent removed under reduced pressure
5. customto afford 13.0 g of crude oil
6. customThis was purified by flash chromatography on silica gel (solvent=80:20 ethyl acetate:heptane)
7. customthe solvent removed in vacuo