Chlorotrimethylsilane → HCID 15137392, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (8.50 ml, 0.0488 mol) and Me3SiCl (3.50 ml, 0.0239 mol) were added to an ice-cold, stirring solution of 1-amino-2-butanethiol (3.00 g, 0.0212 mol) in MeCN (16.0 ml). The solution was stirred 10 minutes at 0°, then treated with more N,N-diisopropylethylamine (3.70 ml, 0.0212 mol) and with a solution of p-nitrobenzyl chloroformate (4.57 g, 0.0212 mol) in MeCN (5.0 ml). The resulting mixture was stirred for 30 minutes at 0° and 90 minutes at room temperature. The mixture was poured into ice-water (50 ml) and extracted with EtOAc (75 ml). The organic phase was separated, washed with 1.25N HCl, 5% NaHCO3, and brine, dried with MgSO4, filtered and evaporated under vacuum to an oil (5.79 g).

Provenance & Evidence