Potassium Carbonate → Methyl 5-methoxy-1-benzofuran-2-carboxylate

HRID 2401482Notes

Reaction equation

HRID 2401482 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CN(C=O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:4][C:3]=2[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-5-methoxy-benzaldehyde (10 g, 65.8 mmol) was stirred in DMF (90 mL) with potassium carbonate (23 g, 0.17 mol) under nitrogen, then methyl bromoacetate was added dropwise. The mixture was stirred at room temperature for 4 h. The reaction was then heated to 80° C. for 18 h. The reaction was allowed to cool then poured onto ice water (200 mL) and the resulting brown suspension was allowed to stir for 30 min. After this time the solid was collected by filtration and washed with water. The solid was dried to afford (5.22 g, 39%), which was taken through to the next step with no further purification.

Workup

  1. temperatureThe reaction was then heated to 80° C. for 18 h
  2. temperatureto cool
  3. additionthen poured onto ice water (200 mL)
  4. stirringto stir for 30 min
  5. filtrationAfter this time the solid was collected by filtration
  6. washwashed with water
  7. customThe solid was dried
  8. customto afford (5.22 g, 39%), which
  9. customwas taken through to the next step with no further purification

Sources & evidence

ORD record
ord-92f9d0582a344f789916b1d8cc7d3d12
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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