3-Methoxybenzaldehyde → HCID 67392783, compound

HRID 907369Notes

Reaction equation

HRID 907369 reaction equation
C(OP([CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])(OCC)=O)C.[H-].[Na+].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1>C1COCC1>[CH3:16][O:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][CH:19]=[C:10](/[CH:9]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 24758Sodium hydrideHCID 54175643HCID 54175643, compound

Product 1

HCID 67392783HCID 67392783, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-[(diethoxyphosphoryl)methyl]benzoate (1.02 g, 3.56 mmol; see step (i) above) in THF (5 mL, dry) under a nitrogen atmosphere was added sodium hydride (0.212 g, 60%, 18.8 mmol). After cooling the reaction mixture to 0° C., m-anisaldehyde (0.485 g, 3.56 mmol) in THF 10 mL, dry) was carefully added dropwise with stirring. The reaction mixture was stirred for 1 h at room temperature and then quenched with water. After neutralisation with dilute HCl, the two layers were separated. The water layer was extracted with ethyl acetate and the organic layers were combined, dried (MgSO4), filtered and the solvent removed under reduced pressure. The product was purified using silica gel column chromatography (RF=0.80 20% ethyl acetate/n-hexane) to give the sub-title compound as a white solid (0.747 g, 78%), m.p.=92-94° C.

Workup

  1. additionwas carefully added dropwise
  2. stirringThe reaction mixture was stirred for 1 h at room temperature
  3. customquenched with water
  4. customAfter neutralisation with dilute HCl, the two layers were separated
  5. extractionThe water layer was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe product was purified

Sources & evidence

ORD record
ord-6f28da79d7af46f39844dae6c75dff41
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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