4-Toluenesulfonyl chloride → HCID 15528413, compound

Participants

Reaction Steps

A solution of Na2CO3 (9.22 g, 86.92 mmol) in water (50 ml) was left under stirring at RT for 20 min prior addition of 2-aminopent-4-en-1-ol (D7) (8.3 g) and EtOAc (160 ml). After 30 minutes stirring, a solution of p-toluenesulfonyl chloride (12.9 g, 67.85 mmol) in EtOAc/THF (24/24 ml) was added over 15 minutes. The reaction mixture was stirred at RT for a weekend. Water (30 ml) and EtOAc (100 ml) were added to the reaction mixture, the phases were separated and the aqueous layer was extracted with EtOAc (2×80 ml). The combined organic phases were evaporated and the residue was purified by Biotage SNAP-Si (100 g) cartridge eluting with a mixture cHex/EtOAc from 80/20 to 50/50. Collected fractions after solvent evaporation afforded the title compound (D8) (5.5 g)

Provenance & Evidence