Tetrabutylammonium Fluoride → 3,5-Bis(hydroxymethyl)benzonitrile

To a solution of 3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile (1.45 g, 3.702 mmol) in tetrahydrofuran (30 mL) at room temperature was added tetrabutylammonium fluoride (9.255 mL, 9.255 mmol, 1 M in tetrahydrofuran). The reaction mixture was stirred at room temperature for 2 h then concentrated in vacuo. The residue was partitioned between ethyl acetate (20 mL) and water (30 mL). The layers were separated and the product was extracted with ethyl acetate (3×20 mL). The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solid was filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 75% ethyl acetate in hexanes yielded 3,5-bis-hydroxymethyl-benzonitrile (465 mg, 77%).

1. concentrationthen concentrated in vacuo
2. customThe residue was partitioned between ethyl acetate (20 mL) and water (30 mL)
3. customThe layers were separated
4. extractionthe product was extracted with ethyl acetate (3×20 mL)
5. washThe organic layers were washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe solid was filtered off
8. concentrationthe filtrate was concentrated in vacuo
9. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
10. washeluting with 75% ethyl acetate in hexanes

ORD record

ord-2930a3fa9f254fc5bebe13fb20df2b71

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06617346B1