2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 87221168, compound

Participants

Reaction Steps

A three necked round bottom flask fitted with a mechanical stirrer, nitrogen inlet and temperature probe was charged with (S)-(−)-2-Methyl-2-Propanesulfinamide (113 g, 0.929 mol) and DCM (2.0 L) at RT (endotherm to 9° C.). Copper(II) Sulfate (309 g, 1.94 mol) was then added followed by (tert-butyldimethylsilyl-oxy)acetaldehyde (150 g, 0.774 mol). After 36 hours the reaction was filtered through a plug of Celite, plug rinsed with DCM (3×200 mL), and concentrated to provide 248 g of the title compound as a light yellow syrup (87 wt %). 1H NMR (CDCl3) δ 8.08 (1H, s), 4.56 (2H, s), 1.22 (9H, s), 0.95 (9H, s), 0.12 (6H, s).

Provenance & Evidence