2-Methyl-2-butene → HCID 66658660, compound

Participants

Reaction Steps

To a suspension of 1-benzyl-2-isopropyl-1H-indole-3-carbaldehyde (Compound 40, 545 mg, 2.0 mmol) in acetonitrile (6 ml), tert-butanol (6 ml) and H2O (12 ml) was added 2-methyl-2-butene (8 ml), potassium phosphate monobasic (5.4 g, 40 mmol), sodium chlorite (80%, 2.3 g, 40 mmol). The mixture was stirred at room temperature for 16 h, more potassium phosphate monobasic (5.4 g, 40 mmol) and sodium chlorite (80%, 2.3 g, 40 mmol) were added and the mixture was stirred at room temperature for an additional 24 h, at which time more potassium phosphate monobasic (5.4 g, 40 mmol), sodium chlorite (80%, 2.3 g, 40 mmol), H2O (8 ml), and 2-methyl-2-butene (8 ml) were added and the mixture was stirred for another 48 h. The solvent was removed in vacuo and the residual solid was washed with CHCl3 (×3) and filtered. The filtrate was concentrated and was purified by flash chromatography on silica gel eluting with 0-20% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-1H-indole-3-carboxylic acid (Compound 41) as a yellow solid.

Provenance & Evidence