Water → HCID 68903078, compound

HRID 1987702Notes

Reaction equation

HRID 1987702 reaction equation
I[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[CH:5][CH:6]=1.[CH3:16][C:17]([CH3:21])([CH3:20])[C:18]#[CH:19].O>N1CCCCC1.[Cu]I.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>[CH3:16][C:17]([CH3:21])([CH3:20])[C:18]#[C:19][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 135123,3-Dimethyl-1-butyneHCID 68901947HCID 68901947, compound

Product 1

HCID 68903078HCID 68903078, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8082PiperidineSolvent

Procedure

To a solution of 2-iodo-5-(2-nitro-phenyl)-thiophene (28 g, 84 mmol) in piperidine (235 ml) were added successively copper(I) iodide (0.8 g, 4.2 mmol), bis(triphenylphosphine)palladium(II) chloride (2.9 g, 4.2 mmol) and 3,3-dimethyl-1-butyne (14 g, 0.17 mol). This mixture was stirred for 16 hours at room temperature. Subsequently, it was poured into 1 litre of water, stirred for 15 minutes and extracted with tert-butyl methyl ether. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated. The remaining oil was purified by silica gel chromatography using ethyl acetate and hexane as eluents, giving Compound No. 6.030.i (22 g).

Workup

  1. stirringstirred for 15 minutes
  2. extractionextracted with tert-butyl methyl ether
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe remaining oil was purified by silica gel chromatography
  7. customgiving Compound No

Sources & evidence

ORD record
ord-75c31950d2234b26bb5ebce09086e159
Source dataset
uspto-grants-2009_06
Patent number
US07553798B2

Reaction notes

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