[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.C(N(CC)CC)C.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1>C1COCC1>[C:18]([O:9][C:6]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:8][CH:7]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1Allomaltol (1.266 g, 10 mmol) was dissolved in 40 mL of anhydrous THF. The mixture was cooled to 0° C. Triethylamine (1.8 mL, 13 mmol) was added. Nicotinoyl chloride hydrochloride (1.988 g, 11 mmol) was added portionwise. Cold bath was removed and the mixture was stirred at room temperature overnight. The reaction was neutralized with ammonia hydroxide then extracted with EtOAc. The organic phase was washed with brine 2 times then dried over Na2SO4 and concentrated. The crude product was purified with flash chromatography using DCM/MeOH to give the desired product as an off-white solid (1.35 g, 58%). MP (148° C.). 1H NMR (CDCl3) δ (ppm): 2.27 (d, 3H, J=0.9 Hz), 6.26 (d, 1H, J=0.9 Hz), 7.42 (dd, 1H, J=4.8, 8.1 Hz), 7.95 (s, 1H), 8.37 (td, 1H, J=1.8, 7.8 Hz), 8.79 (br s, 1H), 9.28 (br s, 1H). 13C NMR (CDCl3) δ (ppm): 19.8, 115.3, 123.8, 124.7, 138.2, 140.8, 148.1, 151.3, 154.1, 162.4, 166.4, 172.4.
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