Butylamine → (Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne
Reaction equation
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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 25 °C
Procedure
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.
Workup
- additionwas added via syringe
- extractionextracted
- washThe combined organic extracts were washed with 50 mL saturated aqueous NaCl
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6ceba3c9637545e49b8b22823bf2fba5
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05198560
Reaction notes
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