Sodium hydride → HCID 57280327, compound

HRID 659118Notes

Reaction equation

HRID 659118 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24].CCOC(C)=O.O>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([F:14])=[C:16]([N+:23]([O-:25])=[O:24])[CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 22728543Water ethylacetate

Product 1

HCID 57280327HCID 57280327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Trimethyl phosphonoacetate (182 mg, 1.00 mmol) in THF (1.70 mL) was added dropwise (caution—vigorous reaction!) to sodium hydride (60% in oil) (60 mg, 1.50 mmol) in THF (1.70 mL) under an atmosphere of nitrogen at 0° C. The reaction mixture was stirred for 15 minutes at 0° C. and then 4-fluoro-3-nitrobenzaldehyde (169 mg, 1.00 mmol) in THF (0.50 mL) was added. After 1 hour, EtOAc/water was added and the organic layer washed with more water, dried (Na2SO4), and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 33% EtOAc in heptane to give the title compound. Yield: 160 mg, 71%; LC-MS 41.31 min; HPLC Purity: >75%; MS (ES+) m/z not detectable (M+H)

Workup

  1. waitAfter 1 hour
  2. washthe organic layer washed with more water
  3. dry with materialdried (Na2SO4)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe crude product was purified by column chromatography
  6. washeluting with 33% EtOAc in heptane

Sources & evidence

ORD record
ord-eefb0711c3a54812886c6d842ce1f53b
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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