Water → Boma

HRID 7725

Reaktionsgleichung

Reaktionsgleichung von HRID 7725
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[O:18][CH3:19].O.[C-:21]#[N:22].[Na+]>CN(C)C=O>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:21]#[N:22])=[C:4]([O:18][CH3:19])[CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Produkt 1

HCID 10192854Boma

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  1. dissolutionto help dissolve solids
  2. customin reaction mixture
  3. customreaction mixture
  4. stirringstir overnight at rt
  5. washby washing
  6. customreaction
  7. extractionwith brine (3×30 mL), extraction with EtOAc
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customremoved solvent in vacuo
  11. customFlash chromatography of resulting orange solid on silica gel using
  12. washa gradient elution of 1:9 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-8e21f0f9208d4b068d738415af301ac5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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