Ethyl Acetate → 5-(2-Hydroxyethyl)-6-vinyl-2-benzofuran-1(3H)-one

HRID 1187080Notes

Reaction equation

HRID 1187080 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13](I)=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[CH:15]([B-](F)(F)F)=[CH2:16].[K+].CCOC(C)=O>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:1][CH2:2][CH2:3][C:4]1[C:13]([CH:15]=[CH2:16])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23679353Potassium vinyltrifluoroborateHCID 666438705-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one

Product 1

HCID 666438955-(2-Hydroxyethyl)-6-vinyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a 500 ml flask containing a stir bar was added 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one (5 g, 16.4 mmol), Potassium vinyltrifluoroborate (3.3 g, 24.7 mmol), Pd(dppf)Cl2 (0.6 g, 0.822 mmol) and TEA (2.3 mL). The mixture was then dissolved in EtOH (50 mL) and heated at 100° C. in a silicon oil bath for 2 h; TLC showed complete reaction. The flask was cooled to room temperature, treated with EtOAc (150 mL) and poured into a separatory funnel and washed with brine (2×100 mL). The organic layer was then separated, dried (Na2SO4), filtered and concentrated to dryness. The resulting organic residue was dissolved in DCM and absorbed into silica gel and purified by MPLC (hexanes/EtOAc; 1/1 eluent) to provide 5-(2-Hydroxyethyl)-6-vinyl-2-benzofuran-1(3H)-one.

Workup

  1. additionTo a 500 ml flask containing a stir bar
  2. customreaction
  3. temperatureThe flask was cooled to room temperature
  4. additionpoured into a separatory funnel
  5. washwashed with brine (2×100 mL)
  6. customThe organic layer was then separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. dissolutionThe resulting organic residue was dissolved in DCM
  11. customabsorbed into silica gel
  12. custompurified by MPLC (hexanes/EtOAc; 1/1 eluent)

Sources & evidence

ORD record
ord-38cc30a89907464fa7c0c57543d404c8
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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