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

HRID 1584918Notes

Reaction equation

HRID 1584918 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-dione

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; 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%].

Workup

  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

Sources & evidence

ORD record
ord-d4198985f5324119b9bbb90a46bbad36
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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