Hydrogen Peroxide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentanol

HRID 328793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 328793
[CH2:1]([O:8][CH:9]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:10][CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CC[O:30]CC.[H-].[OH-].[Na+].OO>O1CCCC1.O>[CH2:1]([O:8][CH:9]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH2:10][CH2:11][CH2:12][OH:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 6

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 166653HydrideHCID 4311764Sodium borohydrideHCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

Produkt 1

HCID 213175844-Benzyloxy-5-(4-fluorophenoxy)-1-pentanolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 4-benzyloxy-5-(4-fluorophenoxy)-1-pentene (2.86 g., 10 mmoles), sodium borohydride (0.47 g., 12.5 mmoles), and tetrahydrofuran (25 ml.) is added dropwise a solution of boron fluoride etherate (2.1 ml., 16.7 mmoles) in tetrahydrofuran (5 ml.) at ice-bath temperatures under a nitrogen atmosphere. The resulting mixture is further stirred at room temperature overnight (ca.15 hours). The reaction flask is chilled in an ice bath and water (2 ml.) is very cautiously added to destory the excess hydride, followed by the additions of sodium hydroxide (5N, 4 ml.) and hydrogen peroxide (30%, 8 ml.). The final mixture is stirred at room temperature for 1/2 hour, diluted with cold water and then extracted with chloroform three times. The combined extracts are washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo leaving the title compound as a viscous oil (3.00 g., 10 mmoles, 100%). ir (neat) 2.97, 3.30, 3.41, 6.22, 6.68, 6.90, 8.03, 8.30, 9.16, 9.44, 12.10, 13.20, 13.60, 14.40μ; pmr (CCl4) δ 1.4-1.9 (4H, m), 3.2-4.2 (6H, m), 4.58 (2H, broad s), 6.6-7.1 (4H, m), 7.20 (5H, s).

Aufarbeitung

  1. temperatureThe reaction flask is chilled in an ice bath
  2. extractionextracted with chloroform three times
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent is evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d303aac951f8465190b9e1df3290c56d
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018802

Notizen zur Reaktion

Wird geladen…