Butylamine → (Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne

HRID 1614726ノート

反応式

HRID 1614726 の反応式
Cl[CH:2]=[CH:3][C:4]#[C:5][CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9].Cl/C=C\C#CC(OCC)OCC.C(N)CCC.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32]>C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu](I)I.C(OCC)C.O>[CH2:8]([O:7][CH:6]([O:10][CH2:11][CH3:12])[C:5]#[C:4]/[CH:3]=[CH:2]\[C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[CH3:9]

参加物

10

反応物 4

HCID 8007ButylamineHCID 66111TrimethylsilylacetyleneHCID 542139675-Chloro-1,1-diethoxy-4-pentene-2-yneHCID 86746680(Z)-5-chloro-1,1-diethoxy-4-pentene-2-yne

生成物 1

HCID 14565407(Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne収率 54%

試薬・触媒・溶媒 5

HCID 83717Copper iodide触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 241Benzene溶媒2 回HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
25 °C

実験手順

A solution of 5-chloro-1,1-diethoxy-4-pentene-2-yne (compound B, 3.8 g, 20 mmol) in 10 mL of benzene was added via cannula to a solution of palladium tetrakis(triphenyl-phosphine) (1.1 g, 0.95 mmol) and copper iodide (0.47 g, 2.46 mmol) in 20 mL benzene stirring at 25° C. under argon. Immediately thereafter, butylamine (4 mL, 40 mmol), followed by trimethylsilylacetylene (5 mL, 40 mmol) was added via syringe. The reaction vessel was wrapped in foil, and the reaction mixture was stirred at 25° C. for 4.25 h. The reaction mixture was poured into 100 mL water and 100 mL diethyl ether and extracted. The aqueous layer was reextracted with 2×40 mL of diethyl ether. The combined organic extracts were washed with 50 mL saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. Flash chromatography over SiO2 using 2%, then 4%, and then 5 % diethylether/pentane as eluent provided the title compound (2.7 g, 54%) as a light brown oil.

後処理

  1. additionwas added via syringe
  2. extractionextracted
  3. washThe combined organic extracts were washed with 50 mL saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6ceba3c9637545e49b8b22823bf2fba5
出典データセット
uspto-grants-1993_03
特許番号
US05198560

反応ノート

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