Sodium hydride → HCID 86751270, compound

HRID 1379584Notes

Reaction equation

HRID 1379584 reaction equation
[OH:1][C:2]1([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[C:15]([F:18])([F:17])[F:16])[CH2:3][C:4]1[N:8]([CH3:9])[CH:7]=[N:6][N:5]=1.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22].[H-].[Na+]>C1COCC1>[CH3:19][C:20]([CH3:25])([CH3:24])[C:21]([O:1][C:2]1([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[C:15]([F:18])([F:17])[F:16])[CH2:3][C:4]1[N:8]([CH3:9])[CH:7]=[N:6][N:5]=1)=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 86751269HCID 86751269, compound

Product 1

HCID 86751270HCID 86751270, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.6 g of 3-(1-hydroxy-2'-trifluoromethylbenzyl)-4-methyl-1,2,4-triazole were dissolved in 20 ml THF, with the aid of sonification. An additional 10 ml THF were added to help dissolve the solid material. The solution was cooled to 0° C. 0.56 g of trimethylacetyl chloride were added slowly and the mixture turned cloudy. After 5 minutes, 0.1 g NaH (60%) added in small portions. The ice/water cooling bath was removed and the reaction mixture was stirred overnight. An additional 0.06 g of NaH was added at room temperature and after another 6 hours, there was no major change. 3 drops of water were added to the cloudy reaction mixture (no hydride was present), followed by diethyl ether. The solid was removed by filtration and washed with diethyl ether. The filtrate was dried (MgSO4), filtered and concentrated to an oil. The oil was purified on a silica gel column by elution with 100% ethylacetate to yield 0.4 g of 3-(1-trimethylacetoxy-2'-trifluoromethylbenzyl)-4-methyl-1,2,4-triazole in the form of an oil.

Workup

  1. dissolutionto help dissolve the solid material
  2. customThe ice/water cooling bath was removed
  3. additionAn additional 0.06 g of NaH was added at room temperature and after another 6 hours
  4. addition3 drops of water were added to the cloudy reaction mixture (no hydride
  5. customThe solid was removed by filtration
  6. washwashed with diethyl ether
  7. dry with materialThe filtrate was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to an oil
  10. customThe oil was purified on a silica gel column by elution with 100% ethylacetate

Sources & evidence

ORD record
ord-fc61396f0b084be687bb708d61aa633f
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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