Reaktion #7821

Reaktionsgleichung

Sodium cyanide

2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

water

→

[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONto help dissolve solids
2. 2
   Sonstigein reaction mixture
3. 3
   Sonstigereaction mixture
4. 4
   workup.STIRRINGstir overnight at rt
5. 5
   Waschenby washing
6. 6
   Sonstigereaction
7. 7
   Extraktionwith brine (3×30 mL), extraction with EtOAc
8. 8
   Trocknendried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeremoved solvent in vacuo
11. 11
    SonstigeFlash chromatography of resulting orange solid on silica gel using
12. 12
    Waschena gradient elution of 1:9 EtOAc

Vorschrift

A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction mixture stir overnight at rt. Workup was done by washing reaction with brine (3×30 mL), extraction with EtOAc, combined organic extracts, dried (Na2SO4), filtered and removed solvent in vacuo. Flash chromatography of resulting orange solid on silica gel using a gradient elution of 1:9 EtOAc:hexanes to 1:3 EtOAc:hexanes afforded the desired intermediate, [4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.36 (m, 7H), 3.99 (s, 3H), 3.74 (s, 2H), 2.59–1.91 (m, 8H). MS (ESI) 265 (M+H)+.

Quelle