Triacetoxyperiodinane → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:12][CH3:13])[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 4-(2-hydroxyethyl)-2-methoxybenzonitrile (1.5 g, 8.5 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added Dess-Martin periodinane (3.6 g, 8.5 mmol) in one portion. The mixture was stirred for 12 h at rt and quenched with a 1:1 mixture of saturated Na2S2O3 (40 mL) and saturated NaHCO3 (40 mL). The resulting mixture was diluted with CH2Cl2 (70 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 2-methoxy-4-(2-oxoethyl)benzonitrile. The residue was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 9.77 (s, 1H), 7.52 (d, 1H, J=8.8 Hz), 6.86 (dd, 1H, J=1.1 Hz), 6.79 (s, 1H), 3.92 (s, 3H), 3.76 (s, 2H); LCMS: [(M+1)]+=176.26; tR=1.98 min.