Sodium Carbonate → Methyl-2-formyl-7-cyclopentyloxybenzo[b]furan-4-carboxylate

HRID 1091864Notes

Reaction equation

HRID 1091864 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH2:14]Br)[O:10][C:9]=2[C:8]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-:23].[Na+].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH:14]=[O:23])[O:10][C:9]=2[C:8]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 66592560Methyl-7-cyclopentyloxy-2-bromomethylbenzo[b]furan-4-carboxylate

Product 1

HCID 24988271Methyl-2-formyl-7-cyclopentyloxybenzo[b]furan-4-carboxylateYield 34,686.699%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of Methyl-7-cyclopentyloxy-2-bromomethylbenzo[b]furan-4-carboxylate (50.0 g, 0.140 moles) in dimethyl sulfoxide (250.0 mL) was added powdered sodium carbonate (22.0 g, 0.21 mmoles) at 105-110° C. and stirred for 2-3 hours. Reaction mixture was cooled to room temperature and diluted with water (2.0 L) and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with water (2×500 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (51 g) as brown viscous oil. Purification by silica gel column using chloroform: ethyl acetate (95:5) as an eluent afforded 21 g of pure product.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. washThe combined organic layers were washed with water (2×500 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of solvent
  6. customgave crude product (51 g) as brown viscous oil
  7. customPurification by silica gel column

Sources & evidence

ORD record
ord-82000aca42b14880841d58ee85e570ce
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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