Cyclopropylacetylene → HCID 86702007, compound

HRID 717979Notes

Reaction equation

HRID 717979 reaction equation
Cl[C:2]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)=[O:3].[C:13]([CH:15]1[CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.CO.[Cu]I>[CH:15]1([C:13]#[C:14][C:2]([C:4]2[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=2)=[O:3])[CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 138823CyclopropylacetyleneHCID 21779986Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate

Product 1

HCID 86702007HCID 86702007, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate (500 mg, 2.443 mmol) was dissolved in triethylamine (5 mL) and the suspension was degassed with nitrogen. Copper(I) iodide (40 mg, 0.210 mmol) and bistriphenylphosphine palladium (II) chloride (40 mg, 0.057 mmol) were added followed by ethynylcyclopropane (162 mg, 2.443 mmol). The mixture was stirred overnight, diluted with methanol and concentrated to dryness. The crude material was partitioned between dichloromethane and water. The organic extracts were dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.

Workup

  1. customthe suspension was degassed with nitrogen
  2. concentrationconcentrated to dryness
  3. customThe crude material was partitioned between dichloromethane and water
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-cbf5339cbc8242349c835f8003b0290c
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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