Benzyl Bromide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

HRID 1833478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833478
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.CO.O.CCCCCC>[CH2:19]([O:12][CH:8]([CH2:7][O:6][C:5]1[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH:10]=[CH2:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

9

Edukt 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 213175735-(4-Fluorophenoxy)-1-penten-4-olHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-penteneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 5-(4-fluorophenoxy)-1-penten-4-ol (9.81 g., 50 mmoles) in dimethylformamide (15 ml.) is added dropwise to a suspension of hexane (2 × 10 ml.) prewashed sodium hydride (50% oil dispersion, 2.64 g., 55mmoles) in dimethylformamide (45 ml.). The resulting mixture is stirred until gas evolution ceases. (A few drops of methanol may be needed to initiate the evolution of hydrogen). The reaction mixture is chilled in an ice bath and treated with a solution of benzyl bromide (10.30 g., 60 mmoles) in dimethylformamide (10 ml.). The reaction mixture is then stirred at room temperature overnight (ca. 16 hours), and then heated on a steam bath for 1 hour. The reaction mixture is diluted with cold water (50 ml.), and extracted with ether four times. The combined extracts are washed with 2N hydrochloric acid and saturated brine and finally dried over anhydrous magnesium sulfate. After the removal of the solvent, the oil residue is vacuum distilled at 112°~6 ° C./0.025 mm. to give the title compound (13.1 g., 45.7 mmoles, 92%). ir (neat) 3.3~3.5, 6.08, 6.21, 6.65, 8.01, 8.28, 9.13, 10.90, 12.10, 13.18, 13.60, 14.40μ; pmr (CCl4)δ2.37 (2H, t, J-5Hz), 3.5-4.0 (3H, m), 4.57 (2H, s), 4.8-5.05 (1H, m), 5.05-5.25 (1H, m), 5.4-6.2 (1H, m), 6.6-7.1 (4H, m), 7.19 (5H, s).

Aufarbeitung

  1. temperatureThe reaction mixture is chilled in an ice bath
  2. stirringThe reaction mixture is then stirred at room temperature overnight (ca. 16 hours)
  3. temperatureheated on a steam bath for 1 hour
  4. extractionextracted with ether four times
  5. washThe combined extracts are washed with 2N hydrochloric acid and saturated brine
  6. dry with materialfinally dried over anhydrous magnesium sulfate
  7. customAfter the removal of the solvent
  8. distillationdistilled at 112°~6 ° C./0.025 mm

Quellen und Nachweise

ORD-Eintrag
ord-93de4d98e6a04ee0ae613cc7f33d4165
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066675

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