Diisobutylaluminum hydride → HCID 19384500, compound

Participants

Reaction Steps

A solution of 30.4 g of 5,6,7,8-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrole-3-carboxylic acid ethyl ester from Example 9, in 300 ml of methylene chloride was treated with 124 ml of a 1.5M DIBAH solution in toluene at 0°-5° C. (ice-water bath) in approximately 20 minutes. After an additional 20 minutes stirring at the same temperature, the reaction mixture was cautiously poured into cold 2N-HCl ice and extracted with methylene chloride. The organic extracts were washed with water and brine, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 28.3 g of a crude yellow oil. Purification of this material on a small silica gel pad (eluting system:hexane-ethyl acetate 1:1) produced 25.8 g (96.2%) of 5,6,7,8-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrole-3-methanol as a yellow oil.

Provenance & Evidence