反应详情

温度

-30 °C

0.68 g of 4-{[6-(methacryloyloxy)hexyl]oxy}benzoic acid (2.20 mM) were dissolved in 20 ml of THF and 2.22 g of triethylamine (22.00 mM). The solution was cooled to −30° C. and 0.25 ml of methansulfochloride (2.20 mM) were added. The mixture was stirred for 1 h at this temperature, then 1.42 g of 4-pentylphenyl 4-{(E)-[4-((E)-{4-[(4-hydroxybenzyl)-amino]1-naphthyl}-diazenyl)-1-naphthyl]diazenyl}-3-methylbenzoate (2.00 mM) were added at once, followed by 50 mg of DMAP. The reaction mixture was stirred for 1 h at −30° C. and was allowed to warm to room temperature while stirred overnight. The next day, 10 g of celite filter aid were added and the resulting suspension was stirred for 15 min., filtered, the cake was washed with THF and the filtrate was evaporated to dryness. The residue was dissolved in 10 ml of dichloromethane and to this solution was then added approx. 30 ml of methanol dropwise at 0° C. The precipitated crystals were filtered off, washed with cooled methanol and dried to give 1.60 g (1.60 mM, 80%) of 4-pentylphenyl 4-[(E)-(4-{(E)-[4-({4-[(4-{[6-(methacryloyloxy)hexyl]oxy}benzoyl)oxy]benzyl}amino)-1-naphthyl]-diazenyl}-1-naphthyl)diazenyl]-3-methylbenzoate as dark crystals; λmax=571 nm, ε=35000 (THF). For total purification, the dye might be flash chromatographed on silica gel.

1. addition0.25 ml of methansulfochloride (2.20 mM) were added
2. stirringThe reaction mixture was stirred for 1 h at −30° C.
3. temperatureto warm to room temperature
4. stirringwhile stirred overnight
5. filtrationThe next day, 10 g of celite filter aid
6. additionwere added
7. stirringthe resulting suspension was stirred for 15 min.
8. filtrationfiltered
9. washthe cake was washed with THF
10. customthe filtrate was evaporated to dryness
11. dissolutionThe residue was dissolved in 10 ml of dichloromethane and to this solution
12. additionwas then added approx. 30 ml of methanol dropwise at 0° C
13. filtrationThe precipitated crystals were filtered off
14. washwashed with cooled methanol
15. customdried