Sodium hydride → 1-(But-3-enyloxy)-4-chloro-2-nitrobenzene

HRID 1373764

Reaktionsgleichung

Reaktionsgleichung von HRID 1373764
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[H-].[Na+].[Cl:8][C:9]1[CH:14]=[CH:13][C:12](F)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1>C1COCC1>[CH2:1]([O:5][C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][C:11]=1[N+:16]([O-:18])=[O:17])[CH2:2][CH:3]=[CH2:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 693893-Buten-1-ol

Produkt 1

HCID 210753581-(But-3-enyloxy)-4-chloro-2-nitrobenzeneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-butene-ol (1.08 mL, 12.53 mmol) in THF (30 mL) at 0° C. was added NaH (60%, 592 mg, 14.81 mmol). The mixture was stirred for 30 minutes, and 4-chloro-1-fluoro-2-nitrobenzene (2 g, 11.39 mmol) in THF (5 mL) was added dropwise. The reaction mixture was further stirred at 0° C. for 2 hours, poured into ice-water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give the desired product (2.5 g, 97%). MS (DCI/NH3) m/z: 244.95 (M+H)+; 1H NMR (400 MHz, DMSO-D6) δ ppm 2.47 (q, J=6.55 Hz, 2 H) 4.22 (t, J=6.60 Hz, 2 H) 5.08 (d, J=10.13 Hz, 1 H) 5.15 (dd, J=17.18, 1.84 Hz, 1 H) 5.80–5.91 (m, 1 H) 7.42 (d, J=9.21 Hz, 1 H) 7.70 (dd, J=9.21, 2.76 Hz, 1 H) 8.00 (d, J=2.76 Hz, 1 H)

Aufarbeitung

  1. stirringThe reaction mixture was further stirred at 0° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2fefd5135d1d46dd8cbd547e7f097c3a
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163939B2

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