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

HRID 1109012Notes

Reaction equation

HRID 1109012 reaction equation
Cl/C=C\Cl.C(OC(OCC)C#C)C.C(N)CCC.Cl/[CH:20]=[CH:21]\[C:22]#[C:23][CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27].[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>[Cu](I)I.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]>[CH2:26]([O:25][CH:24]([O:28][CH2:29][CH3:30])[C:23]#[C:22]/[CH:21]=[CH:20]\[C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[CH3:27]

Participants

8

Reactant 5

HCID 8007Butylamine2×HCID 66111TrimethylsilylacetyleneHCID 662853,3-DiethoxypropyneHCID 643833cis-1,2-DichloroethyleneHCID 86746680(Z)-5-chloro-1,1-diethoxy-4-pentene-2-yne

Product 1

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

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalyst2×HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×

Procedure

The diynene acetal X may be synthesized using the following procedure. Cis-1,2-dichloroethylene is reacted with 3,3-diethoxypropyne in the presence of copper iodide, palladium tetrakis(triphenylphosphine) and n-butylamine, at room temperature and in the absence of light. The product, (Z)-5-chloro-1,1-diethoxy-4-pentene-2-yne is treated with trimethylsilylacetylene in the presence of copper iodide, palladium tetrakis(triphenylphosphine), and n-butylamine at room temperature and away from light to provide (Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne. The corresponding anion is then generated by treatment with an alkali metal hydroxide, such as lithium hydroxide.

Sources & evidence

ORD record
ord-9f7041fc073948ae835d945986c48e83
Source dataset
uspto-grants-1994_06
Patent number
US05318989

Reaction notes

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