Hydrochloric Acid → (+/-)-[trans-3-(3-Trifluoromethylphenyl)-2,2-dimethylcyclopropyl]methanol

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Reaction Steps

The above ester (0.78 g) was dissolved in dichloromethane (12 ml) under nitrogen and cooled to -20°. Diisobutylaluminium hydride (7.4 ml) was added dropwise and the solution stirred at 25° for 18 hours. Careful addition of dilute hydrochloric acid was followed by work up in the usual manner to give (±)-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]methanol (0.31 g). NMR 1H: 7.5(4H,m), 3.65(2H,d), 2.55(1H,bs), 1.62(1H,d), 1.14(1H,m), 1.15(3H,s). 0.90(3H,s).

Provenance & Evidence