Hydrochloric Acid → HCID 59456310, compound

HRID 1873408Notes

Reaction equation

HRID 1873408 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[Se:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=2)=[C:8]([F:19])[C:7]=1[F:20])[CH3:4].[CH3:21]I.Cl>CCCCC.C1COCC1.O>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[Se:16][C:15]([CH2:17][O:18][CH3:21])=[CH:14][CH:13]=2)=[C:8]([F:19])[C:7]=1[F:20])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59456265[5-(4-Ethoxy-2,3-difluorophenyl)selenophen-2-yl]methanol

Product 1

HCID 59456310HCID 59456310, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

400 mg (10.0 mmol) of sodium hydride (60% suspension in paraffin oil) are washed with n-pentane and suspended in 5 ml of THF. A solution of 1.9 g (about 6.0 mmol) of crude [5-(4-ethoxy-2,3-difluorophenyl)selenophen-2-yl]methanol in 20 ml of THF is added dropwise, and the mixture is stirred for 2 h. 1.0 ml (16.1 mmol) of methyl iodide is metered in, and the batch is stirred at RT for 2 h. Water is carefully added to the reaction mixture, which is then acidified using 2 N hydrochloric acid. The mixture is extracted with MTBE, and the extract is washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, toluene). The further purification is carried out by recrystallisation from ethanol and MTBE. 2-(4-Ethoxy-2,3-difluorophenyl)-5-methoxymethylselenophene is obtained as a solid having an m.p. of 84° C.

Workup

  1. stirringis stirred at RT for 2 h
  2. extractionThe mixture is extracted with MTBE
  3. washthe extract is washed with sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by column chromatography (SiO2, toluene)
  7. customThe further purification
  8. customis carried out by recrystallisation from ethanol and MTBE

Sources & evidence

ORD record
ord-ba8b38698f844f7899bd3fff4a12e904
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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