Dimethyl Sulfide → (1-Ethoxyethoxy)acetaldehyde
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[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=C)[CH3:5])[CH3:2].[O:10]=[O+][O-].CSC.C([O-])([O-])=O.[K+].[K+]>O.CCOCC.CO>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=[O:10])[CH3:5])[CH3:2][CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=C)[CH3:5])[CH3:2].[O:10]=[O+][O-].CSC.C([O-])([O-])=O.[K+].[K+]>O.CCOCC.CO>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=[O:10])[CH3:5])[CH3:2]3-[1-(Ethoxy)ethoxy]-1-propene (40 g., 0.0307 mol) was stirred in 100 ml. methanol at -78° for 5.5 hours as O3 was through the solution. The resulting pale blue solution was purged with H2, dimethyl sulfide (34 ml., 43.4 g., 0.68 mol) was added, and the mixture warmed to room temperature over 45 minutes. K2CO3 (0.2 g.) was added, the reaction mixture stripped of solvent, and the residue diluted with 1:1 water:ether. The aqueous layer was separated, diluted with brine and extracted with fresh ether. The organic layers were combined, dried and stripped to yield the title product as an oil, 15.25 g., 1H-nmr: 1.24 (t, 3H), 1.37 (d, 3H), 3.50 (s, 2H), 3.61 (m, 2H), 4.81 (m, 1H), 9.87 (s, 1H).
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