Potassium Carbonate → 3,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether

温度

63 °C

To a stirred solution of 3,5-diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol (0.946 g, 2.7 mmol) in DMF (15 ml) was added K2CO3 (0.746 g, 5.4 mmol) and iododecane (1.632 g, 5.4 mmol). The reaction mixture was warmed to ˜63° C. After ˜20 h, additional K2CO3 (0.373 g, 2.7 mmol) and iododecane (0.816 g, 2.7 mmol) were added. Heating was continued for an additional 20 h followed by stirring at room temperature for ˜20 h. The reaction mixture was concentrated in vac and the residue taken up in EtOAc (50 ml) and water (20 ml). The layers were shaken and separated and the organic layer was washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 5% EtOAc/Hex) to give the product as a brown oil (0.897 g, 68%); 1H NMR (400 MHz, DMSO-d6) δ 0.83–0.88 (m, 3H), 1.20–1.37 (m, 12H), 1.37–1.46 (m, 2H), 1.68–1.76 (m, 2H), 2.71–2.75 (m, 2H), 2.86–2.88 (m, 2H), 3.01 (s, 3H), 4.03 (t, J=6.4 Hz, 2H), 4.22 (s, 2H), 6.87 (s, 2H), 7.34–7.39 (m, 2H), 7.42–7.48 (m, 4H), 7.56–7.60 (m, 4H); IR (film) 2940, 1590, 1460, 1190 cm−1; mass spectrum [(+)ESI], m/z 508 (M+NH4)−.

1. temperatureHeating
2. waitwas continued for an additional 20 h
3. concentrationThe reaction mixture was concentrated in vac
4. stirringThe layers were shaken
5. customseparated
6. washthe organic layer was washed with water (3×10 ml), brine (2×10 ml)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated in vac
10. customdried
11. customThe residue was purified by flash chromatography (hexane and 5% EtOAc/Hex)

ORDレコード

ord-c571059565ef4fdb84a5ce580bdc8123

出典データセット

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07008636B2