[OH:1][CH2:2][CH:3]1[C:12]2[C:7](=[C:8]([C:13]#[N:14])[CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[C:12]2[C:7](=[C:8]([C:13]#[N:14])[CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1)=[O:1]A solution of 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile (210 mg, 1.11 mmol) in 10 mL of anhydrous DCM was added NaHCO3 (933 mg, 11.1 mmol), Dess-Martin reagent (942 mg, 2.22 mmol) at 0° C. The mixture was stirred at 0° C. for 1-2 hours. The reaction mixture was filtrated and purified by prep-TLC to give 4-formyl-3,4-dihydro-2H-chromene-8-carbonitile. 1H-NMR (400 MHz, CDCl3) δ ppm 9.67 (s, 1H), 7.43˜7.45 (m, 1H), 7.34˜7.36 (m, 1H), 6.93˜6.97 (m, 1H), 4.35˜4.39 (m, 1H), 4.0˜4.06 (m, 1H), 3.58˜3.6 (m, 1H), 2.4˜2.46 (m, 1H), 2.06˜2.14 (m, 1H).
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