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

HRID 2090538

反応式

HRID 2090538 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-b755e3dbace041b5a77266796b14546e
出典データセット
uspto-grants-2013_05
特許番号
US08436173B2

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