Hydrochloric Acid → Methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoate

HRID 981266Notes

Reaction equation

HRID 981266 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]1([CH:15]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:16][C:17]([C:19]([C:21]2[C:30]([F:31])=[C:29]([F:32])[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([F:33])[C:22]=2[F:34])=[CH2:20])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CN(C)C=O.O.C(OCC)(=O)C>[C:35]1([CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:16][C:17]([C:19]2([C:21]3[C:22]([F:34])=[C:23]([F:33])[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:29]([F:32])[C:30]=3[F:31])[CH2:4][CH2:20]2)=[O:18])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 15136249Methyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 15136256Methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoateYield 66.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 330 ml of N,N-dimethylformamide was suspended 3.7 g of 60% sodium hydride. To the resulting suspension was added 20.2 g of trimethylsulfoxonium iodide with ice-cooling. The resulting mixture was stirred at room temperature for 1 hour. Thereto was added 33.0 g of methyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5,6-tetrafluorobenzoate. The resulting mixture was stirred at the same temperature for 2 hours. To the reaction mixture were added 300 ml of ethyl acetate and 900 ml of water in this order. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene) to obtain 22.5 g (yield: 66.1%) of methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoate.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred at the same temperature for 2 hours
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue obtained
  8. customwas purified by a column chromatography (eluant: toluene)

Sources & evidence

ORD record
ord-2b089d49eb1b4c6ca019207bb04db48a
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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