Hydrochloric Acid → [1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]methanol

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Reaction Steps

To a suspension of lithium aluminum hydride (6.17 g : 0.163 Mol.) in tetrahydrofuran ( 600 ml) under ice cooling is added 1-trityl-1,2,3- triazol-4-ylcarboxylic acid methyl ester (40.0 g : 0.108 Mol.), and the mixture is stirred at room temperature for 1 hour. To the reaction mixture is added dropwise aqueous tetrahydrofuran under ice cooling. The mixture is neutralized with 10% hydrochloric acid, filtered to remove insoluble material, diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated. The resulting crystals are washed with ether to give 1-trityl-1,2,3-triazol-4-yl- methanol (33.4 g) as white crystals. Yield: 91%. mp. 200° to 201° C. NMR δ (CDCl3) ppm: 2.4-2.9(brs, 1H), 4.76(s, 2H), 7.05-7.15(m, 6H), 7.3-7.4(m, 9H), 7.43(s, 1H).

Provenance & Evidence