HCID 58762434, Verbindung → HCID 58762453, Verbindung

HRID 858561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858561
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1S[C:15](=[O:24])[CH2:16][CH2:17][C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>CCOCC.C1COCC1>[C:18]1([CH2:17][CH2:16][C:15]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Komponenten

5

Edukt 2

HCID 58762434HCID 58762434, VerbindungHCID 178419650HCID 178419650, Verbindung

Produkt 1

HCID 58762453HCID 58762453, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Cyclopentylmagnesium bromide (1.6 mL, 3.15 mmol, 2M soln in ether) was added to a cooled −78° C. solution of 3-Cyclohex-1-enyl-thiopropionic acid S-pyridin-2-yl ester (0.65 g, 2.63 mmol, from Step 3) dissolved in THF (10 mL). The reaction mixture was stirred for 45 min at −78° C. and then warmed up to rt. The reaction was quenched with 1 N HCl and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound as a clear oil (0.39 g, 72%).

Aufarbeitung

  1. temperaturewarmed up to rt
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b538fe3a84614d178d3053b4f9cb81d6
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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