Aluminium lithium hydride → (4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

To a suspension of LiAlH4 (1.76 g, 46.4 mmol) in dry THF (20 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (4.80 g, 15.5 mmol) in THF (30 mL) drop wise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched through the addition of an aqueous solution of HCl (50%; 50 mL) and the resulting mixture was filtered through a bed of celite. The filtrate was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (30 mL) followed by brine (30 mL), dried and concentrated in vacuo to obtain (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (3.6 g, 82.2%). The crude product was pure enough to proceed to the next step without further purification.

1. customThe reaction mixture was quenched through the addition of an aqueous solution of HCl (50%; 50 mL)
2. filtrationthe resulting mixture was filtered through a bed of celite
3. extractionThe filtrate was extracted with ethyl acetate (2×100 mL)
4. washThe combined organic extracts were washed with water (30 mL)
5. customdried
6. concentrationconcentrated in vacuo

ORD record

ord-8e6e7b4ac87b4217970df6a0cc761ae5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691993B2