Triethylamine → Acetaldehyde, 2-(2-phenylethoxy)-
Reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC>CS(C)=O.C(Cl)Cl.CCOCC>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To 2-(2-phenylethoxy)-1-ethanol (0.25 g; 1.5 mmol) [J. Med. Chem., 1570 (1983)] dissolved in DMSO/CH2Cl2 (4 ml/2 ml) is added Et3N (1 ml; 7 mmol) followed by sulfur trioxide pyridine complex (1.2 g; 7.5 mmol). After 10 minutes, the reaction mixture is then diluted with Et2O and washed with brine, 1N HCl, NaHCO3 and brine, dried (MgSO4) and concentrated in yacuo to dryness. The residue is purified by column chromatography using CH2Cl2 to obtain 2-phenylethoxyacetaldehyde which is used directly in Step B.