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

HRID 1092822Notes

Reaction equation

HRID 1092822 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 221459141-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethane-1,2-dioneYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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), in one portion. The resulting mixture is stirred for 1.5 hours, 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%].

Workup

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

Sources & evidence

ORD record
ord-4156af8a53984000a99e5ae565518d04
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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