4-Nitrobenzaldehyde → HCID 10661075, compound

HRID 876114Notes

Reaction equation

HRID 876114 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[PH:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].C[O-].[Na+]>CO>[OH:9][CH:8]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 178476833HCID 178476833, compound

Product 1

HCID 10661075HCID 10661075, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

The title compound was prepared as described in Taylor, W P, et. Al, Bioorg. Med. Chem. 4:1515-1520 (1996). 4-Nitrobenzaldehyde (3.0 g, 19.85 mmol) and diethyl phosphonate (2.74 g, 19.85 mmol) were combined and treated with a 0.5N solution of sodium methoxide in methanol (0.993 mL, 0.496 mmol). The resulting red-orange solution was stirred 12 h at room temperature. The reaction mixture was extracted with dichloromethane (20 mL) followed by half saturated ammonium chloride (20 mL). The organic layer was separated, dried and concentrated under vacuum to provide the title compound as a semi-solid (5.1 g, 89%).

Workup

  1. customThe title compound was prepared
  2. extractionThe reaction mixture was extracted with dichloromethane (20 mL)
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-60e66283f00e4d0dbc2257ade3150d1e
Source dataset
uspto-grants-2015_03
Patent number
US08986740B2

Reaction notes

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