Cornforth reagent → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethane-1,2-dione

HRID 356906

Reaktionsgleichung

Reaktionsgleichung von HRID 356906
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([CH:36]([OH:44])[CH2:37][C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[CH2:26][CH2:25][CH2:24][CH2:23]1>ClCCl>[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([C:36](=[O:44])[C:37]([C:38]3[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=3)=[O:2])[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH2:26]1

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 221458574-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine

Produkt 1

HCID 221459141-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethane-1,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridinium dichromate (3.6 g) in dry dichloromethane (40 mL) under nitrogen is treated with (±)-1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethanol (2.0 g; that is prepared as described in Reference Example 67), in one portion. The resulting mixture is stirred for 1 hour and 30 minutes, and then filtered through a pad of diatomaceous earth, and the pad is washed with diethyl ether. The combined filtrate and ethereal washings are washed with saturated aqueous cupric sulfate solution (2×30 mL), followed by water (30 mL), and then dried over magnesium sulfate. The solvent is removed under reduced pressure, and the resulting oily residue is subjected to flash chromatography on silica gel, eluting with ethyl acetate, to give 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethane-1,2-dione (0.4 g), in the form of a yellow solid, m.p. 117°-119° C. [Elemental analysis: C,70.1; H,6.0; N,4.1%; calculated: C,70.1; H,5.9; N,4.3%].

Aufarbeitung

  1. customthat is prepared
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washthe pad is washed with diethyl ether
  4. washThe combined filtrate and ethereal washings are washed with saturated aqueous cupric sulfate solution (2×30 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bbdafc7dd9e2492fa01ce68c7097cfdd
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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