Triethyl phosphonoacetate → HCID 13952644, compound

HRID 1591803Notes

Reaction equation

HRID 1591803 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>C1COCC1>[CH2:7]([O:6][P:4]([CH:9]([CH2:24][C:23]1[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromide

Product 1

HCID 13952644HCID 13952644, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-(diethoxyphosphoryl)acetate (5.0 ml, 25.2 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 1.10 g, 27.6 mmol) in THF (40 ml) at 0°. After 30 min at room temperature, a solution of 4-nitrobenzylbromide (5.42 g, 25.2 mmol) in THF (40 ml) was added over 30 min. The reaction mixture was stirred for 2 h at room temperature, quenched with water and partitioned between Et2O and water. The aqueous phase was extracted with Et2O and the combined organic layers washed with brine, dried (MgSO4) and evaporated in vacuo. Column chromatography (silica; MeOH/DCM, 1:49) gave the title compound as a pale yellow oil (2.01 g): δH (CDCl3) 8.13 (2H, d, J 8.8 Hz), 7.37 (2H, d, J 8.8 Hz), 4.23-4.06 (1H, m), 3.37-3.20 (3H, m), 1.35 (6H, t, J 7.1 Hz), 1.16 (3H, t, J 7.1 Hz): m/z (EI−, 70V) 360.

Workup

  1. customquenched with water
  2. custompartitioned between Et2O and water
  3. extractionThe aqueous phase was extracted with Et2O
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-939df3d2126244f1b368fa857fe1f300
Source dataset
uspto-grants-2007_11
Patent number
US07291645B2

Reaction notes

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