4-Toluenesulfonyl chloride → rac-Toluene-4-sulfonic acid (1R*,8R*,9R*)-2-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)-ethyl ester

Participants

Reaction Steps

A mixture of 2.0 g of rac-(1R*,8R*,9R*)-9-(2-hydroxy-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol, 1.9 g of TsCl, 1.5 mL of NEt3 and 0.22 g of DMAP in 120 mL of toluene was stirred overnight at rt. The reaction mixture was quenched with water, the organic phase was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by CC with Hept/EtOAc (1:1) to yield 2.7 g of the desired compound as yellow oil.

Provenance & Evidence