Hexane → (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane

HRID 2090538

반응식

HRID 2090538 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]#[C:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.CCCCCC.C([Al]CC(C)C)C(C)C.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Zn+2].[Cl-].O.O1CCCC1>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](/[C:8](/[Si:9]([CH3:10])([CH3:12])[CH3:11])=[CH:7]/[C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:32][CH:31]=1

참가 물질

9

반응물 4

HCID 8058HexaneHCID 696764-IodoanisoleHCID 14643579(5-Methyl-2-thienylethynyl)trimethylsilaneHCID 16682954Dibah

생성물 1

HCID 58159983(Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane수율 66.2%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In a nitrogen atmosphere, (5-methyl-2-thienylethynyl)trimethylsilane (1.0 g, 5.2 mmol) was added to a hexane solution (1.0 mol/L) containing diisobutylaluminum (6.0 ml, 6.0 mmol), followed by stirring at room temperature for 24 hours. The mixture was added to a tetrahydrofuran solution, which contained Pd(PPh3)4 (0.3 g, 0.26 mmol), zinc chloride (1.0 g, 7.3 mmol), and p-methoxyiodobenzene (1.7 g, 7.3 mmol), and which had independently been prepared in another container, followed by stirring in an nitrogen atmosphere at 65° C. for 24 hours. The solution obtained was cooled to room temperature, and water was then added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated sodium chloride solution and then dried with magnesium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1). Thus, (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane (1.0 g, 3.44 mmol) was obtained in a yield of 66%.

후처리

  1. customhad independently been prepared in another container
  2. stirringby stirring in an nitrogen atmosphere at 65° C. for 24 hours
  3. customThe solution obtained
  4. temperaturewas cooled to room temperature
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. filtrationfollowed by filtration
  9. concentrationThe filtrate was concentrated
  10. customa rotary evaporator
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-b755e3dbace041b5a77266796b14546e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436173B2

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