Diisobutylaluminumhydride → 9-(3',5'-Bistrifluoromethylbenzyloxy)nona-2-en-1-ol

Participants

Reaction Steps

7-(3',5'-bistrifluoromethylbenzyloxy)heptan-1-al (See Example 2, 4.97g, 13.96 mmol) was reacted with carboethoxymethylene triphenylphosphorane (4.86g, 13.96 mmol, Lancaster Synthesis Ltd., U.K.) in dry dichloromethane to give ethyl 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2- enoate (5g). The ester (5g, 13.55 mmol) was reacted with diisobutylaluminium hydride (27 mmol) in toluene-dichloromethane at -30°. After conventional work-up, 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2-en-1-ol (4.43g) was obtained. The alcohol was converted into 9-(3',5'-bistrifluoromethylbenzyloxy)nona-2-en-al by Swern oxidation (oxalyl chloride-dimethylsulphoxide, see EP-A-164 187).

Provenance & Evidence