Hydrogen Peroxide → (R)-1-(2',4'-Dichloro-biphenyl-4-yl)-hexane-1,6-diol

HRID 227896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227896
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([OH:21])[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])=[CH:11][CH:10]=1.B(F)(F)F.CC[O:28]CC.[OH-].[Na+].OO.C([O-])([O-])=O.[K+].[K+]>[BH4-].[Na+].COCCOCCOC.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([OH:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:28])=[CH:11][CH:10]=1

Komponenten

9

Edukt 5

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57757255(R)-1-(2',4'-dichloro-biphenyl-4-yl)-hex-5-en-1-ol

Produkt 1

HCID 25061620(R)-1-(2',4'-Dichloro-biphenyl-4-yl)-hexane-1,6-diol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8150DiglymeLösungsmittel2×HCID 4311764Sodium borohydrideLösungsmittel

Versuchsvorschrift

Impure (R)-1-(2′,4′-dichloro-biphenyl-4-yl)-hex-5-en-1-ol (1 g) was dissolved in 0.5 M NaBH4 in diglyme (9 mL) and chilled in an ice bath. BF3.OEt2 (1 mL) in diglyme (4 mL) was added with vigorous stirring. Stirring was continued for 1 hour and water (1 mL) was added. 3 M NaOH (2 mL) was added followed by 30% H2O2 (3 mL). Anhydrous K2CO3 (5 g) was added and the solvent was decanted. The K2CO3 was washed with ethyl acetate and the combined organics were dried (Na2SO4) and evaporated. Distillation under vacuum removed most of the remaining diglyme. The residue was purified by column chromatography (light petroleum:diethyl ether 2:1) to give a clear oil which crystallised on standing to give the title compound as white needles. 13C NMR (CDCl3): δ 25.7, 25.7, 32.6, 39.1, 62.9, 74.3, 125.7, 127.2, 129.5, 129.7, 132.1, 133.2, 133.7, 137.5, 138.7 and 144.6.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. customthe solvent was decanted
  3. washThe K2CO3 was washed with ethyl acetate
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. customevaporated
  6. distillationDistillation under vacuum
  7. customremoved most of the remaining diglyme
  8. customThe residue was purified by column chromatography (light petroleum:diethyl ether 2:1)
  9. customto give a clear oil which
  10. customcrystallised

Quellen und Nachweise

ORD-Eintrag
ord-b8c3fa2dbf1b481391b010440c8960b9
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560597B2

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