Sodium Sulfate → 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline

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Reaction Steps

To a stirred solution of LiAlH4 (1.0 M in THF, 35 mL, 35 mmol), was added a solution of 1a. (2.17 g, 12.4 mmol) in THF (10 mL) for 5 min at 0° C. under nitrogen. The resulting mixture was warmed gradually to reflux, and heated at reflux for 5.5 h. To the cooled mixture with stirring, was added sat'd Na2SO4 dropwise till the complete decomposition of LiAlH4. The mixture was filtered, and rinsed with EtOAc. The organic was washed with H2O, brine, dried (MgSO4), and concentrated to dryness. It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes) to give pure 1b (1.86 g, yield: 93%). LC-MS ESI 162 (M+H).

Provenance & Evidence