Water → Ethyl 6-methoxybenzofuran-3-carboxylate

HRID 1804787Notes

Reaction equation

HRID 1804787 reaction equation
C(OC([C:6]1[O:7][C:8]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=2[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)C.[Cl-].[Na+].O>CS(C)=O>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:8]=2[O:7][CH:6]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 591526576-Methoxy-benzofuran-2,3-dicarboxylic acid diethyl ester

Product 1

HCID 45489697Ethyl 6-methoxybenzofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

6-Methoxy-benzofuran-2,3-dicarboxylic acid diethyl ester (24) (27 g, 92 mmol) is dissolved in 200 ml of a DMSO and the mixture is heated to 170° C. Then sodium chloride (10.7 g, 184 mmol) and water (3.3 ml) are added and the mixture is stirred for 2 h at 160° C. (temperature of reaction mixture). Then the mixture is allowed to cool down and evaporated at high vacuum. The residue is dissolved in ethyl acetate, washed with water and brine and dried over sodium sulfate. Evaporation gave an brown solid, which is further purified by Flash-chromatography (silica gel, ethyl acetate/hexanes 3:7).

Workup

  1. custom(temperature of reaction mixture)
  2. temperatureto cool down
  3. customevaporated at high vacuum
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation
  8. customgave an brown solid, which
  9. customis further purified by Flash-chromatography (silica gel, ethyl acetate/hexanes 3:7)

Sources & evidence

ORD record
ord-6e527b6e68794a11a3a9781d61506c20
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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