Ammonium Chloride → (1R,4R)-4-phenylcyclopent-2-enol

HRID 2404375

Reaktionsgleichung

Reaktionsgleichung von HRID 2404375
C(O[C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH:7]=[CH:6]1)(=O)C.[Cu]C#N.[C:14]1([Mg]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH4+].[Cl-]>C1COCC1>[C:14]1([C@@H:5]2[CH2:9][C@@H:8]([OH:10])[CH:7]=[CH:6]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 98554984-Cyclopentene-1,3-diol, 1-acetate, (1R,3S)-rel-HCID 178418546HCID 178418546, VerbindungHCID 178478979HCID 178478979, Verbindung

Produkt 1

HCID 13613834(1R,4R)-4-phenylcyclopent-2-enolAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (1R,4S)-4-acetoxy-2-cyclopenten-1-ol (491 mg, 3.45 mmol), THF (10 mL), and copper(I) cyanide (93 mg, 1.04 mmol) was cooled to <−20° C. and phenylmagnesium chloride (2.0 M in THF, 5.18 mL, 10.4 mmol) was added at the same temperature. After 10 minutes, TLC (50% EtOAc/hexanes) showed complete conversion. Saturated aqueous NH4Cl (50 mL) was added, extracted with EtOAc (3×50 mL), and dried (Na2SO4) the combined organic layers. Concentrated and purified the residue by flash column chromatography (10-50% EtOAc/hexanes, gradient elution), to provide the title compound (463 mg, 2.89 mmol, 84%). MS (DCI) m/z 143 (M−OH)+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialdried (Na2SO4) the combined organic layers
  3. concentrationConcentrated
  4. custompurified the residue
  5. washby flash column chromatography (10-50% EtOAc/hexanes, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-5fcbdfb42e2d4cc385125cd8f721f81d
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802711B2

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