4-Toluenesulfonyl chloride → HCID 87281347, compound

Participants

Reaction Steps

To a solution of (2S)-4-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol (23.9 g, 108 mmol; second eluting compound in Preparation C, step C.i) and DMAP (2.65 g, 0.2 eq) in DCM (80 mL) cooled to 0° C. were added TEA (43.8 mL, 2.9 eq.) and a solution of TsCl (20.7 g, 1.1 eq.) in DCM (15 mL). The mixture was stirred at rt for 5 h, poured on sat. aq. NaHCO3 and extracted with DCM. The org. layer was dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 2:1) to afford the title intermediate as a colourless oil (31.3 g, 77% yield).

Provenance & Evidence