Carbon Dioxide → HCID 86751271, compound

HRID 1379585Notes

Reaction equation

HRID 1379585 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C([Li])CCC.[C:11](=[O:13])=[O:12].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.[CH3:26][C:27](C)([CH3:31])[C:28](Cl)=O>C1COCC1.CCCCCC>[CH3:26][C:27]([CH3:31])([CH3:28])[C:11]([O:13][C:17]1([CH:20]=[CH:21][CH:22]=[CH:23][CH:16]1[C:15]([F:25])([F:24])[F:14])[CH2:18][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)=[O:12]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 92571H-1,2,4-TriazoleHCID 62493Pivaloyl chlorideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 178418339Butyllithium2×

Product 1

HCID 86751271HCID 86751271, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

1.0 g of 1,2,4-triazole was dissolved in 30 ml THF and cooled with a dry ice bath. As the temperature decreased, a solid fell out of the solution. 5.8 ml of a 2.5M solution of n-butyl lithium in hexane were added while keeping the temperature below -30° C. Upon completion of addition of the butyl lithium, the dry ice bath was replaced with an ice water bath and the reaction mixture was stirred at 0° C. to 4° C. for one hour. The reaction mixture was cooled to -70° C. and 2.7 g of 2-trifluoromethylbenzaldehyde was added. The reaction mixture was allowed to warm up to room temperature overnight. 1.8 g of trimethylacetyl chloride were added, dissolving the solid and giving a yellow-white color to the reaction mixture. The reaction mixture was stirred at room temperature for a total of about 3.5 hours. The reaction mixture was then quenched with ice cold water in an ice bath and extracted twice with diethyl ether. The combined organic layers were dried (MgSO4) and concentrated to an oil. The oil was purified on a silica gel column, eluted with a 1:1 mixture of diethyl ether and hexane, to yield about 1.5 g of 2-(1-trimethylacetoxy-2'-trifluoromethylbenzyl)-1,2,4-triazole.

Workup

  1. temperaturecooled with a dry ice bath
  2. customthe temperature below -30° C
  3. temperatureto warm up to room temperature overnight
  4. dissolutiondissolving the solid
  5. customgiving a yellow-white color to the reaction mixture
  6. stirringThe reaction mixture was stirred at room temperature for a total of about 3.5 hours
  7. customThe reaction mixture was then quenched with ice cold water in an ice bath
  8. extractionextracted twice with diethyl ether
  9. dry with materialThe combined organic layers were dried (MgSO4)
  10. concentrationconcentrated to an oil
  11. customThe oil was purified on a silica gel column
  12. washeluted with a 1:1 mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-7732272325ae4eb38490d40a67ef876c
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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