Methanol → Methyl 5-methoxy-1-benzofuran-2-carboxylate

HRID 1625286Notes

Reaction equation

HRID 1625286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]=2[CH:14]=1.[CH3:15]O.S(Cl)(Cl)=O>O>[CH3:15][O:12][C:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=2[CH:8]=1)=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2886385-Methoxybenzofuran-2-carboxylic acid

Product 1

HCID 14916651Methyl 5-methoxy-1-benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Methoxybenzofuran-2-carboxylic acid (5.04 g, 26 mmol) was weighed into a 200 ml round bottom flask fitted with a stir bar, septum and nitrogen inlet. Anhydrous MeOH (50 ml) was added under nitrogen atmosphere. The solution was cooled in an ice bath and thionyl chloride (2.3 ml, 32 mmol) was added dropwise with vigorous stirring. After stirring for 72 h at room temperature, the reaction mixture was poured into water (150 ml) and the white solid was collected. The solid was dissolved in toluene (100 ml) and the solution was washed with 1M NaHCO3 and brine and dried over MgSO4. Removal of the organic layer provided 5-methoxybenzofuran-2-carboxylic acid methyl ester as a white solid (5.15 g).

Workup

  1. customfitted with a stir bar
  2. temperatureThe solution was cooled in an ice bath
  3. customthe white solid was collected
  4. dissolutionThe solid was dissolved in toluene (100 ml)
  5. washthe solution was washed with 1M NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. customRemoval of the organic layer

Sources & evidence

ORD record
ord-0054b4b8efb14854bd8e10a7511248c8
Source dataset
uspto-grants-2014_07
Patent number
US08779171B2

Reaction notes

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