2-Bromopentane → HCID 86686447, compound

Participants

Reaction Conditions

Reaction Steps

95% NaH (2.15 g, 89.0 mmol) and 5-benzyloxyindole (7) (10.0 g, 44.8 mmol) were added to a schlenk vessel, and the system was evacuated and refilled with nitrogen three times before being cooled to −78° C. DMF (100 mL) was added and the vessel was then cooled with an ice/water bath and kept stirring for another 30 min. 2-Bromopentane (2) (10.2 g, 67.2 mmol) was added dropwise and the resulting mixture was warmed to room temperature slowly and kept stirring overnight. The solvent was removed in vacuo. Toluene (200 mL) was added and the mixture was washed with water (150 mL) and dried with Na2SO4. After solvent was removed in vacuo, the resulting oil was purified using silica column chromatography (1:1 chloroform/hexanes) to give 5-(benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (3.90 g, 30%) as an oil. 1H NMR (500 MHz, CDCl3): δ 7.51 (d, J=7.5, 2H), 7.41 (t, J=8.0 Hz, 2H), 7.35-7.20 (m, 2H), 7.18 (dd, J=8.0, 2.0, 2H), 6.97 (dd, J=9.0, 2.5, 1H), 6.41 (d, J=3.0, 1H), 5.13 (s, 2H), 4.46 (m, 1H), 1.87 (m, 2H), 1.55 (d, J=7.5, 3H), 1.26 (m, 2H), 0.90 (t, J=7.5, 3H). See also Luo, J.; Hart, H.; J. Org. Chem., 52(22): 4833 (1987).

Provenance & Evidence