Benzene → HCID 86750216, compound

HRID 234597Notes

Reaction equation

HRID 234597 reaction equation
[H-].[Na+].C1C=CC=CC=1.[F:9][C:10]([F:30])([F:29])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH:17]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[C:25]([F:28])([F:27])[F:26])[OH:18].[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>CN(C)C=O>[F:28][C:25]([F:27])([F:26])[C:24]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[CH:17]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:10]([F:9])([F:29])[F:30])[O:18][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 241BenzeneHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 19080720HCID 19080720, compound

Product 1

HCID 86750216HCID 86750216, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.029 g of sodium hydride in 20 ml of a 1:1 solution of benzene and dimethylformamide were added 0.25 grams of 1,1-bis-(4-trifluoromethylpyrid-3-yl)methanol. After the gas evolution had subsided, 0.14 grams of pivaloyl chloride were added. After stirring for an hour at 50° C., the reaction mixture was partitioned between 25 ml of water and 50 ml of ethyl ether. The ethyl ether layer was washed with water, washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.24 g of the crude product as a light brown semisolid. This crude material was then purified via chromatography on a silica gel column using ethyl acetate-hexane (1:3) as the eluant to afford 0.2 g of 1,1-bis-(4-trifluoromethylpyrid-3-yl)-1-trimethylacetoxymethane as a light brown solid.

Workup

  1. customthe reaction mixture was partitioned between 25 ml of water and 50 ml of ethyl ether
  2. washThe ethyl ether layer was washed with water
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford 0.24 g of the crude product as a light brown semisolid
  8. customThis crude material was then purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-21f1f54f8df74704af1e012c1d8dc2b6
Source dataset
uspto-grants-1997_01
Patent number
US05595958

Reaction notes

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