Benzaldehyde → 5-Methoxy-3-phenyl-3H-isobenzofuran-1-one

HRID 985147Notes

Reaction equation

HRID 985147 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](NC)=[O:8])=[CH:5][CH:4]=1.C([Li])(CC)C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.C(OCC)(=[O:34])C>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:34])[O:8][CH:18]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 3460314-methoxy-N-methylbenzamide2×HCID 21226206Ethyl acetate hexaneHCID 178418400CID 53628100

Product 1

HCID 131723595-Methoxy-3-phenyl-3H-isobenzofuran-1-oneYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8 (15 g, 91 mmol) in THF was cooled to −70° C. under Argon. To this was added sec-butyllithium (147 mL, 1.3M). After stirring 0.5 h a tan suspension resulted. Added benzaldehyde (9.2 mL, 91 mmol.) and stirred 1 h. Quenched with ice then removed THF in vacuo. Added sat. sodium bicarbonate and extracted with ethyl acetate (4×). Dried the combined organic portions with sodium sulfate (anh.) and removed the solvent in vacuo. Added toluene and heated to reflux for 18 h. Removal of the solvent in vacuo followed by trituration with hexane/ether gave unreacted starting material 8 (4.63 g). Concentration of the filtrate in vacuo followed by flash column chromatography (hexane:ethyl acetate 80:20) gave 9 as a yellow solid (12.0 g, 50.1 mmol, 55.1%)

Workup

  1. customresulted
  2. customQuenched with ice
  3. extractionAdded sat. sodium bicarbonate and extracted with ethyl acetate (4×)
  4. dry with materialDried the combined organic portions with sodium sulfate (anh.)
  5. customremoved the solvent in vacuo
  6. temperatureAdded toluene and heated
  7. temperatureto reflux for 18 h
  8. customRemoval of the solvent in vacuo
  9. customgave unreacted

Sources & evidence

ORD record
ord-cf21ac35805146e3b41953ae232bb7fa
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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