Tetrahydrofuran → Ethyl(6-formyl-1-benzothiophen-3-yl)acetate

HRID 591519Notes

Reaction equation

HRID 591519 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH:15]([OH:18])CO)=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].C1COCC1>O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH:15]=[O:18])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 131734527Ethyl(6-(1,2-dihydroxyethyl)-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734528Ethyl(6-formyl-1-benzothiophen-3-yl)acetateYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl(6-(1,2-dihydroxyethyl)-1-benzothiophen-3-yl)acetate (200 mg), THF (2 mL) and water (2.0 mL) was added NaIO4 (458 mg) at room temperature. The mixture was stirred at room temperature for 30 min. The mixture was quenched with saturated aqueous Na2S2O3 at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with brine twice, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (160 mg).

Workup

  1. customThe mixture was quenched with saturated aqueous Na2S2O3 at room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with brine twice
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-ccbab461fc0d45629378a5f8bfd6c35a
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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