Sodium Hydroxide → Ethanamine, N-(2,2-diethoxyethyl)-2,2-difluoro-

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Reaction Steps

A solution of 3 g (22.5 mM) of 1-amino-2,2-diethoxyethane, 3.1 g (24.8 mM) of difluoroacetaldehyde ethyl hemiacetal and 1 pellet of solid NaOH in 44 ml of toluene was heated at 120° C. with a Dean-Stark trap for 1.5 hours. The mixture is left to stand until it has cooled to room temperature and is concentrated in vacuo. The residue is diluted with 80 ml of methanol, and 3.4 g (90 mM) of sodium borohydride were added in small quantities. The reaction mixture is then stirred overnight, concentrated in vacuo and partitioned between ethyl acetate and water. The organic phase is isolated, dried (MgSO4) and concentrated in vacuo. 3.7 g of crude substance are obtained as a colorless oil. The residue is subjected to a flash chromatography on 40 g of SiO2 (elution with DCM/MeOH, gradient 1-8%). 3.1 g of the desired amine were obtained as a colorless oil.

Provenance & Evidence