Water → HCID 86751264, compound

HRID 1378942Notes

Reaction equation

HRID 1378942 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[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1.[H-].[Na+].[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24].O>C1COCC1>[CH3:21][C:22]([CH3:27])([CH3:26])[C:23]([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[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 86751263HCID 86751263, compound

Product 1

HCID 86751264HCID 86751264, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g of 5-(1-hydroxy-2'-trifluoromethylbenzyl)-pyrimidine (produced according to Example 7) in 15 ml THF at room temperature, 0.2 g of NaH (80%) were added. Gas evolution was observed. After 30 minutes, 0.4 g of trimethylacetyl chloride were added to the reaction mixture and gas evolution was again observed. After 3 hours of stirring, the reaction mixture was worked up with water and the organic materials extracted with diethyl ether. The organic layer was dried (MgSO4), filtered and concentrated to a yellow oil. Elution on a silica gel column with a 1:1 mixture of diethyl ether and hexane yielded 0.56 g of 5-(1-trimethylacetoxy-2'-trifluoromethylbenzyl)-pyrimidine.

Workup

  1. extractionthe organic materials extracted with diethyl ether
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to a yellow oil
  5. washElution on a silica gel column
  6. additionwith a 1:1 mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-336d9a7b0a254bbf87026ffc835d3ed3
Source dataset
uspto-grants-1997_09
Patent number
US05670453

Reaction notes

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