3,4-dihydro-2H-pyran → HCID 12832387, compound

HRID 370773Notes

Reaction equation

HRID 370773 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH: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.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[CH:11][N:10]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][O:22]3)[C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 14100143HCID 14100143, compound

Product 1

HCID 12832387HCID 12832387, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

14.17 g of 4,5-bis(4-methoxyphenyl)imidazole is suspended in 250 ml of absolute 1,2-dichloroethane and combined with 16 g of 3,4-dihydro-2H-pyran as well as 0.5 ml of tin tetrachloride. The mixture is heated to reflux under agitation for 12 hours, then allowed to cool, and poured into 500 ml of cold sodium bicarbonate solution. The organic phase is separated, dried over sodium sulfate, and concentrated under vacuum. The residue is dissolved in dichloromethane and subjected to hexane precipitation. The sediment is dissolved in ether. The solution is clarified with activated carbon, concentrated under vacuum, and made to crystallize, thus producing 15.03 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole, mp 127°-128°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under agitation for 12 hours
  3. temperatureto cool
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue is dissolved in dichloromethane
  8. customsubjected to hexane precipitation
  9. dissolutionThe sediment is dissolved in ether
  10. concentrationconcentrated under vacuum
  11. customto crystallize

Sources & evidence

ORD record
ord-3c5a9e0568434c42b285d4ca0a356685
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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