Water → 5-(2-Trifluoromethylphenyl)-4-pentynenitrile

HRID 440981

反応式

HRID 440981 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1I.[C:12](#[N:17])[CH2:13][CH2:14][C:15]#[CH:16].C(N(CC)CC)C.O>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:16]#[C:15][CH2:14][CH2:13][C:12]#[N:17]

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 1405604-Cyano-1-butyne

生成物 1

HCID 199555385-(2-Trifluoromethylphenyl)-4-pentynenitrile収率 92.9%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

Under a nitrogen atmosphere, a solution of 15.0 grams (0.055 mole) of 2-trifluoromethylphenyl iodide, 4.8 grams (0.061 mole) of 4-pentynenitrile, 30.6 mL (0.22 mole) of triethylamine, 0.4 gram (0.0006 mole) of bis(triphenylphosphine)palladium(II) chloride, and 0.1 gram (0.0006 mole) of copper(II) iodide in 50 mL of acetonitrile was stirred at ambient temperature for 5 hours. After this time, gas chromatographic analysis (GC) of the reaction mixture indicated that the reaction was about 60% complete. The reaction mixture was warmed to 40°-45° C., where it was stirred for 16 hours. After this time the reaction mixture was poured into 300 mL of water, and the mixture was extracted with two 100 mL portions of diethyl ether. The combined extracts were washed with aqueous dilute hydrochloric acid and then were dried with magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 1:1-methylene chloride and petroleum ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 11.4 grams of 5-(2-trifluoromethylphenyl)-4-pentynenitrile. The NMR spectrum was consistent with the proposed structure.

後処理

  1. temperatureThe reaction mixture was warmed to 40°-45° C.
  2. extractionthe mixture was extracted with two 100 mL portions of diethyl ether
  3. washThe combined extracts were washed with aqueous dilute hydrochloric acid
  4. dry with materialwere dried with magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated under reduced pressure to a residual oil
  7. washElution
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9a62fb6a39604dc586b353f75b6b63db
出典データセット
uspto-grants-1996_05
特許番号
US05521192

関連ノート

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