Carbon Dioxide → HCID 20080504, compound

HRID 1653810Notes

Reaction equation

HRID 1653810 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([C:31]#[N:32])C(O)=O)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(=O)=O>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:31]#[N:32])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 20080540HCID 20080540, compound

Product 1

HCID 20080504HCID 20080504, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

67.5 g of 7-[4,5-bis(4-methoxyphenyl)-2-oxazolyl]-2-cyanoheptanoic acid are heated to 180° C. until the evolution of carbon dioxide has ceased (7 hours). After cooling, the residual oil is dissolved in 400 cm3 of ethyl ether. The ethereal solution is washed with 3 times 50 cm3 of saturated aqueous sodium bicarbonate solution and 100 cm3 of water, dried over magnesium sulphate and filtered, and the solvent is removed. The evaporation residue is chromatographed on a column 5.8 cm3 in diameter containing 360 g of silica gel (50 to 200μ). The column is eluted, collecting 250 cm3 fractions, with 3.5 liters of a diisopropyl ether/ethyl acetate (70:30 by volume) mixture. The fractions emerging at between 0.5 and 3.5 liters are concentrated to dryness. 52.3 g (75.9%) of 7-[4,5-bis(4-methoxyphenyl)-2-oxazolyl]heptanenitrile are thereby obtained in the form of an oil, which is used directly in the above reaction.

Workup

  1. custom(7 hours)
  2. temperatureAfter cooling
  3. washThe ethereal solution is washed with 3 times 50 cm3 of saturated aqueous sodium bicarbonate solution and 100 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. customThe evaporation residue is chromatographed on a column 5.8 cm3 in diameter
  8. additioncontaining 360 g of silica gel (50 to 200μ)
  9. washThe column is eluted
  10. customcollecting 250 cm3 fractions
  11. concentrationare concentrated to dryness

Sources & evidence

ORD record
ord-50143102130e475bb770d2db0d47de75
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

Loading…