3,3,3-Triethoxyprop-1-yne → Ethyl 2-(3-fluoro-2-(3,3,3-triethoxyprop-1-ynyl)phenyl)acetate

HRID 2078239Notes

Reaction equation

HRID 2078239 reaction equation
[F:1][C:2]1[C:3](I)=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:15]([O:17][C:18]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])[C:19]#[CH:20])[CH3:16]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[F:1][C:2]1[C:3]([C:20]#[C:19][C:18]([O:21][CH2:22][CH3:23])([O:17][CH2:15][CH3:16])[O:24][CH2:25][CH3:26])=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 109209723,3,3-Triethoxyprop-1-yneHCID 67099443Ethyl 3-fluoro-2-iodophenylacetate

Product 1

HCID 67099522Ethyl 2-(3-fluoro-2-(3,3,3-triethoxyprop-1-ynyl)phenyl)acetateYield 35.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Bis(triphenylphosphine)palladium(II) chloride (456 mg, 0.649 mmol), cuprous iodide (371 mg, 1.95 mmol), and ethyl 2-(3-fluoro-2-iodophenyl)acetate (2.0 g, 6.49 mmol), were mixed in a 20 mL microwave tube. The tube was sealed, and ACN (12 mL) and TEA (6 mL) were added. The mixture was placed under argon atmosphere and 3,3,3-triethoxyprop-1-yne (1.68 g, 9.74 mmol) was added via syringe. The reaction was heated at 60° C. for 16 hours, cooled to room temperature, and concentrated under vacuum. The residue was purified by flash chromatography to give 820 mg of ethyl 2-(3-fluoro-2-(3,3,3-triethoxyprop-1-ynyl)phenyl)acetate as a yellow oil.

Workup

  1. customThe tube was sealed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c6cbdaf76e4844168771db1a07cb28b7
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…