Tetrahydrofuran → 2-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene

HRID 1873403Notes

Reaction equation

HRID 1873403 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[Se:20][C:19]([CH:21]=O)=[CH:18][CH:17]=2)=[C:12]([F:23])[C:11]=1[F:24])[CH3:8].[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.CC(OC)(C)C.O.Cl>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[Se:20][C:19]([CH:21]=[CH:29][CH2:25][CH2:26][CH3:27])=[CH:18][CH:17]=2)=[C:12]([F:23])[C:11]=1[F:24])[CH3:8]

Participants

8

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

Product 1

HCID 722902592-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene

Reagents, catalysts & solvents 4

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4.12 g (10.3 mmol) of butyltriphenylphosphonium bromide are initially introduced in 50 ml of THF at 0° C., and 1.04 g (9.27 mmol) of potassium tert-butoxide dissolved in 7 ml of THF are added. After 1.75 h at RT, 2.27 g (7.20 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added in one portion with ice-cooling, and the batch is stirred at RT for 6 h. 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:EtOAc=5:1-2:1). 2-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene is obtained as an orange oil.

Workup

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

Sources & evidence

ORD record
ord-29b3bc6ef66940c59fb84b98a0603d0a
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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