Tetrahydrofuran → Methyl 2-(3-methoxy-phenyl)-7-benzofuranacetate

HRID 1646966Notes

Reaction equation

HRID 1646966 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]3[C:17](C=O)=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.CSS(C)(C)=O.[O:26]1[CH2:30]C[CH2:28][CH2:27]1.C(=O)(O)[O-:32].[Na+]>Cl.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:28][C:27]([O:26][CH3:30])=[O:32])[CH2:13][CH:12]=[C:14]3[CH:15]=[CH:16][CH:17]=[C:11]3[O:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 149956822-(3-Methoxy-phenyl)-7-benzofurancarbaldehyeHCID 178505373HCID 178505373, compound

Product 1

HCID 67875966Methyl 2-(3-methoxy-phenyl)-7-benzofuranacetate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7.4 g of the product of Step A, 4.4 g of methyl methylsulfinyl methyl sulfide, 75 ml of tetrahydrofuran and 7 ml of Triton B was refluxed for one hour and then was poured into water and extracted with dichloromethane. The extracts were dried and concentrated to obtain 10 ml of produce which was dissolved in a 2N hydrochloric acid solution in methanol. The solution was stirred for 24 hours, treated with sodium bicarbonate, and stirred for one hour. After separating, extraction was carried out with ether and the extracts were washed and concentrated to obtain 9 g of product which was chromatographed on silica to obtain (eluant: hexane-ethyl acetate (9-1)) 4.3 g of the desired product which was used as is.

Workup

  1. temperaturewas refluxed for one hour
  2. extractionextracted with dichloromethane
  3. customThe extracts were dried
  4. concentrationconcentrated
  5. customto obtain 10 ml
  6. customof produce which
  7. stirringstirred for one hour
  8. customAfter separating
  9. extractionextraction
  10. washthe extracts were washed
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-576f0007ad29438ab02c83b87e8a3219
Source dataset
uspto-grants-1993_01
Patent number
US05182295

Reaction notes

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