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

HRID 1278840Notes

Reaction equation

HRID 1278840 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]([C:17]#[CH:18])([CH3:16])[CH3:15].[CH2:19]1COCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([C:7]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[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 trimethylsilylacetylene (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-7717bc734c1f4d6da17da5227d18228c
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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