Lithium borohydride → (7-Aminochroman-2-yl)methanol

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Reaction Steps

A solution of ethyl 7-amino-2-chromancarboxylate (1.26 g, 5.7 mmol) in anhydrous THF is treated dropwise with lithium borohydride (2.0 M in THF, 13.7 mmol), stirred under nitrogen at ambient temperatures for 4 h, quenched with methanol, stirred at ambient temperatures for 1 h, poured into water, extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo to afford the title compound as a nearly colorless oil, 0.9 g (90% yield), identified by NMR and mass spectral analyses.

Provenance & Evidence