Water → 6-(Benzyloxy)-5-methoxy-1H-indole-2-carbaldehyde

Participants

Reaction Steps

To a solution of the ester (56) (1.0 g, 3.22 mmol) prepared as described in example 248 in tetrabydrofuran (10 mL) was added a suspension of lithium aluminum hydride (0.150 g, 3.86 mmol) in tetrahydrofuran (10 mL) dropwise, the reaction mixture was stirred at room temperature for 20 min. Water (1 mL) was added dropwise and then dilute sodium hydroxide (1 mL) was added, the solution was stirred for 10 min and then filtered through Celite and concentrated. The resulting yellow oil was dissolved in chloroform (20 mL) and then manganese dioxide (2.2 g, 26.0 mmol) was added, the reaction mixture was heated at 50° C. for 1 h and then filtered through Celite and concentrated. The residue was recrystallized from dichloromethane to give 6-(benzyloxy)-5-methoxy-1H-indole-2-carbaldehyde (57) (0.74 g, 82%) as pale yellow needles. Found: C, 72.53; H, 5.42; N, 4.92. C17H15NO3 requires: C, 72.58; H, 5.37; N, 4.98.

Provenance & Evidence