Potassium tert-butoxide → HCID 72290249, compound

HRID 1873442Notes

Reaction equation

HRID 1873442 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Te:14][C:13]([CH:15]=O)=[CH:12][CH:11]=2)=[C:6]([F:17])[C:5]=1[F:18])[CH3:2].[CH3:19][C:20](C)([O-])C.[K+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1.CC(OC)(C)C.O.Cl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Te:14][C:13]([CH:15]=[CH:19][CH3:20])=[CH:12][CH:11]=2)=[C:6]([F:17])[C:5]=1[F:18])[CH3:2]

Participants

8

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59456309HCID 59456309, compound

Product 1

HCID 72290249HCID 72290249, compound

Reagents, catalysts & solvents 5

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

6.0 g (16.0 mmol) of ethyltriphenylphosphonium bromide are initially introduced together with 5.2 g (14.3 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)-tellurophene-2-carbaldehyde in 150 ml of THF at 0° C., and 0.89 g (7.9 mmol) of potassium tert-butoxide dissolved in 7 ml of THF is added. After 2 h at room temperature, the mixture is diluted with MTBE, and water and 2 N hydrochloric acid are added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene=3:2). Further purification is carried out by recrystallisation from ethanol; 2-(4-ethoxy-2,3-difluorophenyl)-5-propenyltellurophene is obtained as a yellowish solid.

Workup

  1. additionis added
  2. additionare added
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted with MTBE
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. customand dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene=3:2)
  9. customFurther purification
  10. customis carried out by recrystallisation from ethanol

Sources & evidence

ORD record
ord-c32f2ec7ebec4d3ba551dade2f700f77
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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