Potassium Carbonate → Methyl 6-(phenylmethoxy)-2-benzofurancarboxylate

HRID 1907760Notes

Reaction equation

HRID 1907760 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]2[CH:13]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[O:17][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 12082973Methyl 6-(phenylmethoxy)-2-benzofurancarboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-(benzyloxy)-2-hydroxybenzaldehyde (10 g, 43.9 mmol) in DMF (60 mL), was added methyl bromoacetate (48.3 mmol, 4.57 mL), and potassium carbonate (24.2 g, 175.6 mmol). The solution was heated to 80° C. and stirred for 16 h. The reaction was quenched with water (100 mL) and aqueous extraction was performed with AcOEt (2×50 mL). The organic phase was dried with sodium sulfate and concentrated. Purification was achieved via silica gel chromatography employing 0-30% AcOEt in hexane gradient. This afforded 393 as a light yellow solid (4.5 g, 37%).

Workup

  1. customThe reaction was quenched with water (100 mL) and aqueous extraction
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-a5a79144b3ca470f8bdca805db65fcc9
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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