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8. Conversion of sorbitol to isosorbide. Typical experimental
procedure (Table 1, entry 1): A mixture of sorbitol 1 (200.0 mg,
1.01 mmol) and Nafion NR-50 (44.1 mg) in [TMPA][NTf2] (2.689
g) was stirred and heated to 180 °C by microwave irradiation for
10 min. The residue was dissolved in MeOH (10 mL) and the
MeOH solution was combined with the filtrate. The resulting
organic solution was concentrated in vacuo. The filtrate was
concentrated and water (30 mL) was added. The water solution
was extracted with CH2Cl2 (10 × 30 mL). The organic phase was
dried over Na2SO4. Filtration and concentration gave
[TMPA][NTf2] in 98% recovery (2.622 g). The water phase was
concentrated in vacuo. The residue was subjected to flash
chromatography (silica gel/EtOAc-MeOH 20:1 v/v) to give
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1
sorbitol 2 in 65% yield (98.4 mg). H NMR (500 MHz, D2O) δ
4.51 (t, J = 4.6 Hz, 1H), 4.36 (d, J = 4.2 Hz, 1H), 4.27 (td, J = 6.9,
5.0 Hz, 1H), 4.20 (d, J = 2.8 Hz, 1H), 3.84 – 3.77 (m, 2H), 3.74
(dd, J = 10.5, 3.2 Hz, 3H), 3.36 (dd, J = 9.0, 7.5 Hz, 1H); 13
NMR (126 MHz, D2O) δ 87.3, 81.4, 75.5, 75.1, 71.8, 71.1.
C
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Quantification of product 2 and 3 by HPLC was carried out by the
following method. Fluctose (201.3 mg) as the internal standard
was added to the residue of concentrated water phase and the
mixture was dissolved by water (10 mL). This solution was
analyzed by HPLC column (Waters X-bridgeAmide, 3.5 m, 4.6
mm id × 100 mm, CH3CN-water 70:30, 0.6 mL/min, detected by
JASCO RI2031plus RI detector).
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