Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → (R)-1-(4-isobutylphenyl)pentan-1-ol

HRID 1034096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034096
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1>O1CCCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([OH:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)boraneHCID 109984904'-Isobutylpentanophenone

Produkt 1

HCID 11074925(R)-1-(4-isobutylphenyl)pentan-1-olAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4'-Isobutylpentanophenone (2.1 g) was added to a solution of (+)-B-chlorodiisopinocampheylborane (3.57 g) in tetrahydrofuran (7 ml) at -25° C. After stirring for 5 hours, the solvent was removed and the residue was dissolved in ethyl ether (30 ml). To this solution was added diethanolamine (2 ml), and the mixture was stirred for 2 hours. The solid was filtered off and washed with ethyl ether. The combined filtrates were concentrated and the residue was chromatographed on silica gel (hexane:dichloromethane =1:2) to give (R)-1-(4-isobutylphenyl)pentan-1-ol (635 mg).

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl ether (30 ml)
  3. additionTo this solution was added diethanolamine (2 ml)
  4. stirringthe mixture was stirred for 2 hours
  5. filtrationThe solid was filtered off
  6. washwashed with ethyl ether
  7. concentrationThe combined filtrates were concentrated
  8. customthe residue was chromatographed on silica gel (hexane:dichloromethane =1:2)

Quellen und Nachweise

ORD-Eintrag
ord-2f76a18addf04736869fc8be51318c07
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05312829

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