Reaktion #62687

Reaktionsgleichung

4-(2-tetrahydropyran-2-yloxyethyl)phenol

K2CO3

3-bromopropanol

→

1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(3-hydroxypropy)benzene

Ausbeute 73.6%

Lösungsmittel

2-butanone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.)

Quelle