Sodium hydride → HCID 131718226, compound

Participants

Reaction Steps

To a slurry of sodium hydride (12 g, 0.3 mol, 60% dispersion in oil) in DMF (200 mL) was added dropwise a solution of 5-bromoindole (50 g, 0.255 mol) in DMF (300 mL). After stirring for 15 minutes 2-t-butyldimethylsilyloxyethyl bromide (60 g, 0.255 mol, neat) was added dropwise and the reaction mixture stirred for 1 hour. The reaction mixture was partitioned between ice water and ethyl ether. The organic fraction was washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by column chromatography (silica, 3:1 hexane/acetone) to give 68.6 g of the title compound as a light yellow oil. 1H NMR (CDCl3) δ:7.72 (s, 1 H); 7.1-7.3 (m, 3 H); 6.4 (d, 1 H); 4.18 (t, 2 H); 3.86 (t, 2 H); 0.8 (s, 9 H); -0.18 (s, 6 H).

Provenance & Evidence