Hydrochloric Acid → 2-(3-Methoxyphenyl)-cyclopentanol

HRID 377305

Reaktionsgleichung

Reaktionsgleichung von HRID 377305
[O:1]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH:2]12.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([Mg]Br)[CH:12]=[CH:13][CH:14]=1.C(OCC)(=O)C.Cl>O1CCCC1.[Cu]Cl>[OH:1][CH:3]1[CH2:4][CH2:5][CH2:6][CH:2]1[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([O:8][CH3:7])[CH:14]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 178490745HCID 178490745, Verbindung

Produkt 1

HCID 27596482-(3-Methoxyphenyl)-cyclopentanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of a mixture of 1,2-epoxycyclopentane (7.0 g) and copper(I) chloride (260 mg) in tetrahydrofuran (70 ml) was added 3-methoxyphenylmagnesium bromide (53.5 m mol) in tetrahydrofuran (60 ml) at -78° C. under N2. The mixture was stirred for 1 hour at 0° C. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid and then the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give 1-hydroxy-2-(3-methoxyphenyl)-cyclopentane (13 g).

Aufarbeitung

  1. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3474d8f17eb34a109a738bd51f4697eb
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025375

Verknüpfte Notizen

Wird geladen…