[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][C:8](=[O:12])SCC)[C:4](=[O:13])[O:3]1.C([SiH](CC)CC)C>C(Cl)Cl.[Pd]>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][CH:8]=[O:12])[C:4](=[O:13])[O:3]1(R)—S-Ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (22.5 g, 103 mmol) was dissolved in CH2Cl2 (500 mL), purged with nitrogen and 10% palladium on carbon (2.19 g, 2.06 mmol) was added and triethylsilane (24.7 mL, 155 mmol) was dissolved in CH2Cl2 (20 mL) and added dropwise through an addition funnel over 30 minutes and stirred at ambient temperature overnight under nitrogen. The reaction was filtered through celite, concentrated and purified over silica gel (10 to 40% EtOAc in hexanes) to afford (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetaldehyde (16 g, 101 mmol, 98.1% yield) as a clear colorless oil.
Loading…
