2-Iodothiophene → HCID 57483695, compound

HRID 1944114Notes

Reaction equation

HRID 1944114 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].I[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1>C(NC(C)C)(C)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH3:2]

Participants

5

Reactant 2

HCID 189212-IodothiopheneHCID 662853,3-Diethoxypropyne

Product 1

HCID 57483695HCID 57483695, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 7912DiisopropylamineSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of propargylaldehyde diethyl acetal (405 mg) in diisopropylamine (8 ml) were added 2-iodothiophene (1.2 g) and copper(II) acetate monohydrate (66.4 mg). The suspension was flushed with a stream of N2. Pd(PPh3)4 (75 mg) was added, the reaction mixture was flushed with nitrogen again. The suspension was stirred for 1 h at 55° C. A precipitate was formed and it was necessary to dilute the reaction mixture with diisopropylamine (6 ml) to keep it stirring. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1/0→17/3 (v/v)] as eluent.

Workup

  1. customThe suspension was flushed with a stream of N2
  2. additionPd(PPh3)4 (75 mg) was added
  3. customthe reaction mixture was flushed with nitrogen again
  4. customA precipitate was formed
  5. stirringstirring
  6. filtrationThe reaction mixture was filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel in heptane/ethyl acetate [1/0→17/3 (v/v)] as eluent

Sources & evidence

ORD record
ord-b4305dd5af2a448d844aa50df9c54ff0
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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