Water → Ethyl 3-(4-(methoxymethoxy)phenyl)propiolate

HRID 884060

Reaction equation

HRID 884060 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14].O>CN(C=O)C.[Cu-]=O>[CH3:11][O:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12182Ethyl propiolateHCID 110327301-Iodo-4-(methoxymethoxy)benzene

Product 1

HCID 57693052Ethyl 3-(4-(methoxymethoxy)phenyl)propiolateYield 52%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Under an Ar atmosphere, a mixture of 1-iodo-4-(methoxymethoxy)benzene (500 mg, 1.89 mmol), Ethyl propiolate (371 mg, 3.78 mmol) and Copper(I) oxide (270 mg, 1.89 mmol) in DMF (10 ml) was heated at 110° C. for 16 h. After cooling, H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 15:1) gave 2e (52%). 2e: colorless oil; 1H-NMR (CDCl3) δ 1.36 (3H, t, J=7.1), 3.48 (3H, 2), 4.29 (2H, q, J=7.1), 5.20 (2H, s), 7.02 (2H, d, J=8.8 Hz), 7.54 (2H, d, J=8.8 Hz).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with AcOEt
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel flash column chromatography (eluent: hexane/AcOEt, 15:1)

Sources & evidence

ORD record
ord-9cfb2d551c5f45b49a43cd506448d58f
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Linked notes

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