Tetrahydrofuran → HCID 86583978, compound

HRID 413937Notes

Reaction equation

HRID 413937 reaction equation
[Cl:1][C:2]1(C#C)[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH2:3]1.[C:11](OCC)(=O)[C:12]#[C:13][CH3:14].C[O:20]C1C=CC=C(OC)C=1P(C1C(OC)=CC=CC=1OC)C1C(OC)=CC=CC=1OC.[CH2:50]1[CH2:54][O:53][CH2:52][CH2:51]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:54]([O:53][C:52](=[O:20])/[CH:51]=[C:13](\[CH3:14])/[C:12]#[C:11][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([Cl:8])[CH:5]=1)[CH3:50]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 78043Ethyl 2-butynoateHCID 2734597Tris(2,6-dimethoxyphenyl)phosphineHCID 87842257HCID 87842257, compound

Product 1

HCID 86583978HCID 86583978, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of 1,3-dichloro-phenyl acetylene (6.07 g, 35.5 mmol) in dry THF (60 mL) was added palladium acetate (186 mg, 0.68 mmol), ethyl 2-butynoate (5.97 g, 53.2 mmol) and tris (2,6-dimethoxyphenyl)phosphine (316 mg, 0.68 mmol) at room temperature. The reaction mixture was stirred for 18 h and filtered. The filtrate was washed with water (10 mL), and the water phase was extracted with ether (10 mL). The combined organic phases were dried and evaporated. The residue was purified by column chromatography using heptane:THF (20:1) as eluent. (E)-3-Methyl-5-(3,5-dichloro-phenyl)-pent-2-en-4-ynoic acid ethyl ester was isolated in 4.65 g (46%) yield.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water (10 mL)
  3. extractionthe water phase was extracted with ether (10 mL)
  4. customThe combined organic phases were dried
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-126689e2f1ed42579ce4619070a7149b
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Reaction notes

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