Triethylamine → HCID 20245338, compound

Participants

Reaction Conditions

Reaction Steps

A solution of α-ethenyl-1,3-dioxolane-2-propanol (49.4 g, 315 mmole) in dichloromethane (175 ml) was treated sequentially with dimethylaminopyridine (5.72 g, 47 mmole) and triethylamine (52.8 ml, 380 mmole) followed by (dropwise) a solution of t-butylchlorodiphenylsilane (89.5 g, 332 mmole) in dimethylformamide (150 ml). The reaction was stirred under argon for 48 hours (25° C.), poured into 2.5 L of ice water and extracted with ethyl acetate (1.2 L). The organic extracts were wsashed with water (2×1 L), brine (1 L), dried (sodium sulfate), filtered, and concentrated in vacuo to 130 g of viscous yellow oil. The crude product was dissolved in ether, filtered from a small amount of suspended material, concentrated in vacuo, and chromatographed (Waters, Prep 500 L.C., 10% ethyl acetate:hexane) to afford 106 g of the title compound.

Provenance & Evidence