Ethanol → Ethyl(6-vinyl-1-benzothiophen-3-yl)acetate

HRID 591517Notes

Reaction equation

HRID 591517 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].[CH3:24][CH2:25]O>[Cl-].[Na+].O.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]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH:24]=[CH2:25])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 57443344Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734526Ethyl(6-vinyl-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate (600 mg) and EtOH (10 mL) were added potassium vinyl(trifluoro) borate (240 mg), PdCl2(dppf) (119 mg) and TEA (0.454 mL) at room temperature, and the mixture was heated to 110° C. with microwave irradiation for 15 min. The mixture was poured into brine at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, and dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (320 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dd7bf1db8b574898864e57273b719aa9
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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