Tetrahydrofuran → 2-Pent-1-ynylaniline

HRID 1640251Notes

Reaction equation

HRID 1640251 reaction equation
C1COCC1.I[C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].C(N(CC)CC)C.[CH:21]#[C:22][CH2:23][CH2:24][CH3:25]>C(OCC)C.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.[Cu](I)I>[C:21]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])#[C:22][CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 119952-IodoanilineHCID 123091-Pentyne

Product 1

HCID 109317192-Pent-1-ynylaniline

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

20 mL THF were placed in the flask and degassed with argon. Then 2.3 g (10 mmol) 2-iodo-aniline, 0.72 g (1.0 mmol) PdCl2(PPh3)2 and 0.20 g (1.0 mmol) copper iodide were added and the flask was rinsed with argon. Then 4.2 mL (30 mmol) triethylamine and 1.5 mL (15 mmol) 1-pentyne were added. The reaction mixture was stirred for 3 h at RT, diluted with diethyl ether, filtered through kieselguhr and evaporated down.

Workup

  1. customdegassed with argon
  2. washthe flask was rinsed with argon
  3. filtrationfiltered through kieselguhr
  4. customevaporated down

Sources & evidence

ORD record
ord-606b7ed71ede4474b3854063538babd4
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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