1-Naphthaldehyde → HCID 53411263, compound

To a solution of 1-naphthaldehyde (2.2 ml, 16.0 mmol) in tetrahydrofuran (6 ml) was added 2,2-diethoxyethanamine (2.9 ml, 20.0 mmol) and the mixture was stirred at room temperature 0.5 hr. And then sodium triacetoxyborohydride (10.6 g, 50 mmol) was added and the mixture was stirred for additional 4 hr. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate (5 g) and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=100:0 to 70:30) to obtain the title compound (3.0 g, 46%).

1. stirringthe mixture was stirred for additional 4 hr
2. washwashed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml)
3. dry with materialThe organic layer was dried over magnesium sulfate (5 g)
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo
6. customthe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=100:0 to 70:30)

ORD record

ord-400204c8f1db4402b3fc50808d4f3666

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126981B2