Calcium Carbonate → 6-[3-[4-(1-Pyrrolidinyl)phenyl]propoxy]-2-hexanone

HRID 1721965

Reaktionsgleichung

Reaktionsgleichung von HRID 1721965
[CH3:1][C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)SCCCS1.C(=O)([O-])[O-:28].[Ca+2]>C1COCC1.CO.O.[Hg](Cl)Cl>[N:22]1([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:2](=[O:28])[CH3:1])=[CH:17][CH:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

6

Edukt 2

HCID 10112Calcium CarbonateHCID 198627331-[4-[3-[4-(2-Methyl-1,3-dithian-2-yl)butoxy]propyl]phenyl]pyrrolidine

Produkt 1

HCID 198627016-[3-[4-(1-Pyrrolidinyl)phenyl]propoxy]-2-hexanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24085Mercuric ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of the product of stage (iv) (3.2 g) in THF (50 ml) was added to a stirred suspension of mercury (II) chloride (8.5 g) and calcium carbonate (3.2 g) in methanol-water (9:1, 50 ml) and the mixture was stirred at reflux for 1 h. The reaction was filtered through hyflo, the filtrate was concentrated in vacuo and the resulting oil was dissolved in chloroform (50 ml). The resulting precipitate was removed by filtration, the solvent was evaporated and the residue was purified by FCC (System D 19:1→4:1) to give the title compound as a crystalline mass (1.4 g) m.p. 30°-31°.

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. filtrationThe reaction was filtered through hyflo
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionthe resulting oil was dissolved in chloroform (50 ml)
  5. customThe resulting precipitate was removed by filtration
  6. customthe solvent was evaporated
  7. customthe residue was purified by FCC (System D 19:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f2ef6d99d184d2296edef7dfc469a1a
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853381

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