Tetrahydrofuran → Ethyl 3-phenyl-5-trimethylsilanylpent-2-en-4-ynoate

HRID 897067

Reaction equation

HRID 897067 reaction equation
[C:1]1([C:7]#[C:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][Si:14]([CH3:18])([CH3:17])[C:15]#[CH:16].[CH2:19]1COCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([C:7]([C:16]#[C:15][Si:14]([CH3:18])([CH3:17])[CH3:13])=[CH:8][C:9]([O:11][CH2:12][CH3:19])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 66111TrimethylsilylacetyleneHCID 138378Phenylpropynoic acid methyl ester

Product 1

HCID 86142661Ethyl 3-phenyl-5-trimethylsilanylpent-2-en-4-ynoate

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A solution of TDMPP (1.4 g) and palladium acetate (700 mg) in THF (200 ml) is stirred for 15 min at room temperature and methyl phenylpropiolate (10 g, 62.5 mmol) is then added. The reaction medium is stirred for 5 min at room temperature and trimethyl-silylacetylene (87.5 mmol) is then added. Stirring is continued overnight at room temperature. The reaction medium is concentrated and filtered through silica.

Workup

  1. stirringStirring
  2. waitis continued overnight at room temperature
  3. concentrationThe reaction medium is concentrated
  4. filtrationfiltered through silica

Sources & evidence

ORD record
ord-61eae75c5d7947aeb1d138ab049b4db4
Source dataset
uspto-grants-2005_07
Patent number
US06921777B2

Linked notes

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