Ethyl Acetate → [4-(1,3-Benzoxazol-2-yl)-2-(methoxymethoxy)phenyl]acetonitrile

HRID 7715

Reaktionsgleichung

Reaktionsgleichung von HRID 7715
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][CH2:19][O:20][CH3:21].[C-:22]#[N:23].[Na+].CCOC(C)=O>CN(C=O)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:22]#[N:23])=[C:4]([O:18][CH2:19][O:20][CH3:21])[CH:5]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 219909422-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

Produkt 1

HCID 21990994[4-(1,3-Benzoxazol-2-yl)-2-(methoxymethoxy)phenyl]acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Versuchsvorschrift

2-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole (250 mg, 0.72 mmol) was treated with sodium cyanide (150 mg, 2.2 mmol) in DMF/H2O (15 mL/1.5 mL) at 90° C. for 3 h and EtOAc (150 mL) was added. The EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was eluted with flash column (silica gel, hexanes:EtOAc 4:1) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-(methoxymethoxy)phenyl]acetonitrile as a yellow solid. 1H NMR (CD3OD, 300 MHz), δ 8.02 (d, 2H), 7.95 (m, 1H), 7.80 (m, 1H), 7.63 (m, 1H), 7.57 (d, 2H), 7.40 (m, 2H). MS (ESI) 295 (M+H)+.

Aufarbeitung

  1. washThe EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe residue was eluted with flash column (silica gel, hexanes:EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-1bb2abbd51504100ae8fddcf2916a41c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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