Triethylamine → 1-(2-Cyclopropylethynyl)-4-methoxybenzene

HRID 408503Notes

Reaction equation

HRID 408503 reaction equation
[CH:1]1([C:4]#[CH:5])[CH2:3][CH2:2]1.I[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCCC1.[Cu]I>[CH:1]1([C:4]#[C:5][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 696764-IodoanisoleHCID 138823Cyclopropylacetylene

Product 1

HCID 586098031-(2-Cyclopropylethynyl)-4-methoxybenzeneYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylethyne (15 g, 0.22 mol) was slowly added to a mixture of 4-iodoanisole (30. g, 0.13 mol), copper (I) iodide (1.2 g, 0.0063 mol), and triethylamine (30. g, 0.30 mol) in tetrahydrofuran (THF, 400 mL). After being stirred for 4 hours, the resulting precipitate was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by column chromatography to afford 1-cyclopropylethynyl-4-methoxy-benzene as a yellow oil (15 g, 0.087 mol, 67%). 1H NMR (CDCl3): δ 7.31 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.8 Hz, 2H), 3.79 (s, 3H), 1.43 (m, 1H), 0.85 (m, 2H), 0.78 (m, 2H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with THF
  3. customThe combined filtrate was evaporated to dryness
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-446f236127514355b9cc86f95a1a0d0d
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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