Electric Literature of 874-97-5,Some common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, molecular formula is C8H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
e 2-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester Diethyl azodicarboxylate (174 mg, 1.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxyphenyl ester (285 mg, 1.0 mmol), as prepared in the preceding step, 3-cyanobenzyl alcohol (133 mg, 1.0 mmol)(Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (263 mg, 1.0 mmol) in tetrahydrofuran (10 mL) at 0 C. The mixture was stirred at 0 C. for 2 hours and at room temperature for 3 hours. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3*30 mL). The organic phase was washed with saturated NaHCO3 (2*30 mL), brine (2*30 mL) and dried over Na2 SO4. The solvent was removed in vacuo the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a pale yellow oil (375 mg, 93%). 1 H-NMR (300 MHz, CDCl3) delta 5.02 (s, 2H), 6.78 (m, 2H), 6.85 (dd, 1H, J=4.2, 1.3 Hz), 7.20 (t, 1H, J=8.2 Hz), 7.38 (t, 1H, J=5.8 Hz), 7.51 (t, 1H, J=7.7 Hz), 7.59-7.68 (m, 5H) and 7.93 (dd, 1H, J=4.0, 0.7 Hz).
The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US6034127; (2000); A;,
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