[F:1][C:2]1[C:3]([CH2:12][CH2:13][OH:14])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[F:1][C:2]1[C:3]([CH2:12][CH:13]=[O:14])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]To a solution of 5-fluoro-4-(2-hydroxyethyl)-2-methoxybenzonitrile (175 mg, 0.900 mmol) in Dichloromethane (4 mL) was added Dess-Martin Periodinane (0.53 g, 1.2 mmol). The solution was stirred for 2 h at ambient temperature, then was diluted with NaHCO3 (sat.) and Na2S2O3 (sat.) and stirred for 30 min. The layers were separated and the aqueous layer was extracted with dichloromethane twice. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired aldehyde, which was used directly without further purification.
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