Magnesium → 1-(3-Benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol

HRID 1030335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030335
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[C:21]([F:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OC1C=C(Br)C=C(F)C=1)C1C=CC=CC=1.[Mg]>O1CCCC1>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:4]2([OH:8])[CH2:5][CH2:6][CH2:7][CH:3]2[O:2][CH3:1])[CH:20]=[C:21]([F:23])[CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 5462224MagnesiumHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 124766872-Methoxycyclopentan-1-oneHCID 178505958HCID 178505958, Verbindung

Produkt 1

HCID 193879111-(3-Benzyloxy-5-fluorophenyl)-2-methoxycyclopentanolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

After repetition of the above reaction, a solution of 2-methoxycyclopentanone (12.5 g) in tetrahydrofuran (10 ml) was added to a solution of 3-benzyloxy-5-fluorophenylmagnesium bromide [prepared by heating a mixture of 3-benzyloxy-5-fluorobromobenzene (31 g), magnesium powder (2.65 g) and tetrahydrofuran (20 ml) to 40° C. for 2 hours] and the mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and water. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained, as a mixture of diastereoisomers, 1-(3-benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol (21.7 g, 62%), as an oil.

Aufarbeitung

  1. customAfter repetition of the above reaction
  2. customprepared
  3. temperatureby heating
  4. customThe mixture was evaporated
  5. customthe residue was partitioned between diethyl ether and water
  6. washThe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. additiona 9:1 v/v mixture of methylene chloride and diethyl ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ff65bcf37386441492d57627b0ec2137
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05105020

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