反应详情

温度

90 °C

5.15 g (28 mmol) 8 were dissolved in 15 mL DMF (anhydrous, Aldrich) and added to a suspension of 15.5 g (112 mmol, 4 eq.) K2CO3 in 25 mL DMF under nitrogen atmosphere. 13.4 mL (112 mmol, 4 eq.) iso-pentyl bromide were added. The thick, canary-yellow reaction mixture was heated to 90° C. and became stirrable again. It was left at this temperature for at least 8 h. Product formation could be followed by TLC (hexanes/ethyl acetate 9:1, Rf (product)=0.85). After cooling to r.t., DMF was removed with a vacuum rotovap, then ethyl acetate and water were added. After phase separation, the water layer was extracted with ethyl acetate two more times, the organics were pooled, washed with brine, dried with MgSO4, concentrated and put under vacuum overnight. The crude product was purified by column chromatography (hexanes/ethyl acetate 9:1), yielding 5.15 g (80%) of a yellow liquid. 1H NMR (CDCl3) δ 8.42 (dd, J1=1.5 Hz, J2=2.4 Hz, 1H), 7.90 (t, J1=2.4 Hz, J2=2.4 Hz, 1H),7.87 (dd, J1=1.5 Hz, J2=2.4 Hz, 1H), 4.40 (t, J=6.7 Hz, 2H, PhOCH2CH2CH(CH3)2), 4.11 (t, J=6.6 Hz, 2H, PhOCH2CH2CH(CH3)2), 1.93-1.65 (m, 6H), 0.99 (d, J=6.6 Hz, 12H, 2×CH(CH3)2); 13C NMR (CDCl3) 164.38, 159.51, 148.94, 132.69, 121.46, 116.10, 112.87, 67.40, 64.42, 37.38, 37.08, 24.97, 24.77, 22.29; ESI-MS m/z 360 [M+K−2]+, 408 [M+2Na+K], 669 [M2+Na]+.

1. waitIt was left at this temperature for at least 8 h
2. temperatureAfter cooling to r.t.
3. customDMF was removed with a vacuum rotovap
4. additionethyl acetate and water were added
5. customAfter phase separation
6. extractionthe water layer was extracted with ethyl acetate two more times
7. washwashed with brine
8. dry with materialdried with MgSO4
9. concentrationconcentrated
10. customput under vacuum overnight
11. customThe crude product was purified by column chromatography (hexanes/ethyl acetate 9:1)