Methyl propiolate → HCID 64534769, compound

HRID 1808866Notes

Reaction equation

HRID 1808866 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15]>CN(C=O)C.[Cu-]=O>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:3]#[C:2][C:1]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 13536Methyl propiolateHCID 68257o-Iodoanisole

Product 1

HCID 64534769HCID 64534769, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of methyl propiolate (2, 1.314 ml, 15.41 mmol) and copper(I) oxide (1.086 g, 7.59 mmol) in DMF (20 ml) was added 1-iodo-2-methoxybenzene (1, 1.262 ml, 9.48 mmol). The resulting mixture was heated in a Microwave reactor to 110° C. for 2 hrs. The reaction mixture was filtered through a short pad of silica gel and washed w/EtOAc. The organic layer was washed w/1M HCl, brine and sat'd NaHCO3, dried (Na2SO4) and concentrated to leave an oil as crude product, which was purified by flash chromatography (SiO2, EtOAc/Hexane, 1:2) to afford methyl 3-(2-methoxyphenyl)propiolate 3 (932 mg, 4.66 mmol, 49.1% yield). 1H-NMR (500 MHz, CDCl3), δ: 7.54 (1H, dd), 7.44 (1H, td), 6.98-6.92 (m, 2H), 3.92 (s, 3H), 3.86 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of silica gel
  2. washwashed w/EtOAc
  3. washThe organic layer was washed w/1M HCl, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto leave an oil as crude product, which
  7. customwas purified by flash chromatography (SiO2, EtOAc/Hexane, 1:2)

Sources & evidence

ORD record
ord-6f08fe2ba9364ba8b33cb82838853cd5
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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