Toluene → 1-(Aminomethyl)-2,3-dihydro-6-methoxy-1H-inden-1-ol

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Reaction Steps

60 g of trimethylsilyl cyanide are added via syringe to a mixture of 75 g of 6-methoxy-1-indanon, 0.8 g of anhydrous zinc iodide and 150 milliliters of anhydrous toluene. The reaction mixture was heated to 60 degrees Centigrade for 6 hours and then stirred for 16 hours without heating. To a cooled suspension of 44 g of lithium aluminium hydride in 1300 milliliters of anhydrous ether was added the solution of the unpurified cyanohydrin in ether at 0°-5° C. After the addition had been completed the reaction mixture was refluxed with stirring for 21/2 hours. After cooling destruction of the excess lithium aluminium hydride was completed by cautious dropwise addition of 45 milliliters of water followed by dropwise addition of 45 milliliters of 14% sodium-hydroxide solution and subsequent addition of 190 milliliters of water. Stirring was continued for 30 minutes. Filtration and extraction with dichloromethane gave a clear organic solution which was dried over anhydrous magnesium sulphate and evaporated, and the residue was crystallized from ether. Yield: 58 grams of product.

Provenance & Evidence