Water → 7-Cyclopentyloxy-2-methylbenzo[b]furan-4-carboxaldehyde

HRID 1091860Notes

Reaction equation

HRID 1091860 reaction equation
[OH:1][C:2]1[C:7]2[O:8][C:9]([CH3:11])=[CH:10][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:20]1(Br)[CH2:24][CH2:23][CH2:22][CH2:21]1.O>CN(C=O)C>[CH:20]1([O:1][C:2]2[C:7]3[O:8][C:9]([CH3:11])=[CH:10][C:6]=3[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 824109927-Hydroxy-2-methylbenzo[b]furan-4-carbaldehyde

Product 1

HCID 442478827-Cyclopentyloxy-2-methylbenzo[b]furan-4-carboxaldehydeYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred suspension of 7-Hydroxy-2-methylbenzo[b]furan-4-carbaldehyde (39.0 g, 0.221 moles) in DMF (200 mL) was added powdered potassium carbonate (76.0 g, 0.555 moles) and cyclopentyl bromide (43.0 g, 0.287 moles) and stirred at 70-75° C. for 4-5 hrs. The reaction mixture was then cooled to room temperature and water (1.5 L) was added to it. The organic material separated was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water ((2×500 mL) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave product (55.0 g) as light brown viscous oil.

Workup

  1. stirringstirred at 70-75° C. for 4-5 hrs
  2. customThe organic material separated
  3. extractionwas extracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with water ((2×500 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent under vacuo

Sources & evidence

ORD record
ord-8c78252483404a70b1bf8d53ef0a93f6
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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