Sodium hydride → HCID 10502067, compound

HRID 1736244Notes

Reaction equation

HRID 1736244 reaction equation
[F:1][C:2]1[C:3]([O:20][CH2:21][O:22][CH3:23])=[C:4]([C:10]([NH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[C:3]([O:20][CH2:21][O:22][CH3:23])=[C:4]([C:10]([N:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 24758Sodium hydride3×HCID 25517Ammonium ChlorideHCID 62493Pivaloyl chloride3×HCID 10806525HCID 10806525, compound

Product 1

HCID 10502067HCID 10502067, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The above ethyl 3,5-difluoro-6-(N-ethoxycarbonylamino)-2-methoxymethoxybenzoate was dissolved in 35 mL of tetrahydrofuran under ice-cooling, 792 mg of sodium hydride (60% oil dispersion) and 1.69 mL of pivaloyl chloride were added and the mixture was stirred at 0° C. for 25 minutes. 396 mg of sodium hydride (60% oil dispersion) and 0.85 mL of pivaloyl chloride were further added and the mixture was stirred at 0° C. for 20 minutes. 158 mg of sodium hydride (60% oil dispersion) and 0.34 mL of pivaloyl chloride were further added and the mixture was stirred 0 ° C. for 1.2 hours. An aqueous saturated solution of ammonium chloride was added to the reaction solution and the mixture was extracted with ether. The organic layer was washed with an aqueous saturated solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 6.63 g of ethyl 3,5-difluoro-6-(N-ethoxycarbonyl-N-pivaloylamino)-2-methoxymethoxybenzoate (two stage yield: 80%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 0° C. for 20 minutes
  3. stirringthe mixture was stirred 0 ° C. for 1.2 hours
  4. extractionthe mixture was extracted with ether
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4367ed21876c4091abedfc6beaeddaf5
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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