Diisobutylaluminum hydride → (1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) acetaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of ester from Step 2 (16.0 g, 39.8 mmol) in CH2Cl2 (320 mL) at -100° C. was added slowly a solution of DIBAH (1.5M/toluene, 32 mL, 47.7 mmol). The reaction was then stirred for 1-- h at -78° C., before being quenched by the addition of MeOH (3 mL), followed by 25% w/v tartaric acid (100 mL). After stirring overnight at r.t., the product was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and evaporated to give a pale green syrup. This was stirred vigorously with 1:4 Et2O/hexane to give 13 g of the title compound as an off-white solid.

Provenance & Evidence