Hexane → HCID 69832482, compound

Participants

Reaction Steps

A solution of imidazole-1-sulfonic acid dimethylamide (1.96 g, 0.0112 mol, prepared according to D. J. Chadwick and R. I. Ngochindo J. Chem. Soc. Perkin Trans. I (1984) 481) in dry tetrahydrofuran (90 ml) under nitrogen was cooled to −78° C. and treated dropwise with 15% n-butyllithium in hexane (8.2 ml, 0.01393 mol). After 30 minutes tert-butyldimethylsilyl chloride (2.1 g, 0.01393 mol) in dry tetrahydrofuran (5 ml) was added and the mixture was allowed to warm to room temperature. After 1.5 hr the mixture was again cooled to −78° C. and treated with 15 % n-butyllithium in hexane (8.5 ml, 0.01360 mol). After 30 minutes 3-phenyl-1-indanone (3.40 g, 0.01633 mol) in dry tetrahydrofuran was added and the mixture was allowed to warm to room temperature during the night. The mixture was quenched with saturated sodium carbonate solution and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and washed twice with water, dried, filtered and concentrated under reduced pressure. Purification was done by flash chromatography (elution with a heptane—ethyl acetate gradient).

Provenance & Evidence