[CH3:1]/[C:2](/[CH2:6][CH2:7][CH2:8][CH3:9])=[CH:3]\[CH2:4][OH:5].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1]/[C:2](/[CH2:6][CH2:7][CH2:8][CH3:9])=[CH:3]\[CH:4]=[O:5]To a suspension solution of alcohol 13b (739 mg, 5.7 mmol), 4 Å molecular sieves (2.9 g, activated), and NMO (1.33 g, 11.4 mmol) in CH2Cl2 (12 mL) at 0° C., was added TPAP (120 mg,0.34 mmol) in one-portion. The resulting dark reaction mixture was allowed to stir at 0° C. for 30 min, before being diluted with CH2Cl2 (20 mL), and then filtered through a short pad of silica gel. The filtrate was concentrated in vacuo to afford aldehyde 14c (704 mg, 98% yield) as a colorless oil. The aldehyde is sufficiently pure for immediate use without further purification:
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