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

HRID 1614726노트

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HRID 1614726 반응식
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]

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 83717Copper iodide촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 241Benzene용매2회HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ceba3c9637545e49b8b22823bf2fba5
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198560

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