4-Nitrobenzaldehyde → HCID 10661075, compound

HRID 1947879Notes

Reaction equation

HRID 1947879 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].[P:12]([O-:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>C1COCC1>[CH2:14]([O:13][P:12]([CH:8]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)[OH:9])(=[O:19])[O:16][CH2:17][CH3:18])[CH3:15]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 3780918Diethylphosphite

Product 1

HCID 10661075HCID 10661075, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of p-nitrobenzaldehyde (3.022 g, 20 mmol), diethyl phosphite (2.762 g, 20 mmol), and MgO (2.0 g, 49.6 mmol) in THF (30 mL) was stirred at room temperature for 5 days. The reaction mixture was filtered, the filtrate was concentrated, and residue was purified by silica gel chromatography (EtOAc/hexanes: 1:4) to give 4.53 g of diethyl[(4-nitrophenyl)(hydroxy)methyl]phosphonate (yield: 78%). 1H NMR (CDCl3, 400 MHz): δ=1.27 (m, 6H), 4.08-4.18 (m, 4H), 5.18 (d, J=12.0 Hz, 1H), 7.67-7.70 (m, 2H), 8.24 (dd, J=0.8, 8.8 Hz, 2H). MS (ES+): m/z 290.07 [MH+]. HPLC: tR=1.15 min (UPLC TOF, polar—3 min). This material (4.53 g) was hydrogenated in the presence of 10% Pd/C (200 mg) in MeOH (20 mL) under 1 atmosphere for 4 h. The catalyst was filtered off, filtrate was concentrated, and the residue was purified by silica gel chromatography (2% MeOH in DCM) to afford 3.93 g of the title compound (yield: 72%). MS (ES+): m/z 242.08 [MH+—H2O]. HPLC: tR=0.8 min (UPLC TOF, polar—3 min).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customresidue was purified by silica gel chromatography (EtOAc/hexanes: 1:4)

Sources & evidence

ORD record
ord-294382096e0443e3bb400c53bcc71236
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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