Chlorosuccinimide → HCID 89526536, compound

Participants

Reaction Steps

To a solution of methyl 3-[(1-{[tert-butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-5-yl)sulfonyl]propanoate (140 mg, 0.35 mmol) in THF (1 mL) was added sodium methoxide (0.70 mL, 0.5 M, 0.35 mmol). The reaction mixture was stirred for 20 minutes, then the solvents were removed under reduced pressure and the residue was stripped down from heptanes to generate a white foam. This foam was suspended in DCM (2 mL) at 0° C. and then NCS (47 mg, 0.35 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was quenched by the addition of brine (2 mL) and the phases were separated using a phase separator. The aqueous layer washed with DCM, and the combined organic layers were concentrated under reduced pressure. The crude concentrate was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

Provenance & Evidence