Iodoethane → HCID 21999890, compound

HRID 1975942Notes

Reaction equation

HRID 1975942 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:5]=1[CH3:11])[CH3:2].OC1C=CC(I)=CC=1C.C(I)C.C([O-])([O-])=O.[K+].[K+].[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC(C)=O.CN(C=O)C>[CH3:35][O:34][C:30](=[O:33])/[CH:31]=[CH:32]/[C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH3:11])[CH:6]=1

Participants

9

Reactant 6

HCID 6340IodoethaneHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 1437134-Iodo-2-methylphenolHCID 21999882HCID 21999882, compound

Product 1

HCID 21999890HCID 21999890, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

In a 250 mL RBF was charged 2-ethoxy-5-iodotoluene (5 g, 19.1 mmol, prepared from 2-hydroxy-5-iodotoluene by reacting with ethyl iodide in acetone in the presence of K2CO3), methyl acrylate (17 mL), P(o-tolyl)3 (1.16 g), DMF (25 mL) and TEA (25 mL). The mixture was degased under nitrogen. To the solution was added Pd(OAc)2 (0.43 g) and the mixture was heated to reflux under nitrogen for 20 hours. After cooling to room temperature, the reaction mixture was diluted with water (200 mL) and extracted with ether (2×250 mL). The ether extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography. Eluting with 5-20% ethyl acetate in hexanes afforded the desired product 11 (3.3 g).

Workup

  1. customThe mixture was degased under nitrogen
  2. additionTo the solution was added Pd(OAc)2 (0.43 g)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen for 20 hours
  5. additionthe reaction mixture was diluted with water (200 mL)
  6. extractionextracted with ether (2×250 mL)
  7. washThe ether extracts were washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by silica gel chromatography
  12. washEluting with 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8659fce6ab2740f09d6758056cfe393c
Source dataset
uspto-grants-2001_05
Patent number
US06225288B1

Reaction notes

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