Sodium hydride → HCID 86602647, compound

HRID 2100609Notes

Reaction equation

HRID 2100609 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[CH2:14]([C:16]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH:31]=O)[CH:17]=1)[CH3:15]>C1COCC1.O>[CH2:14]([C:16]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18](/[CH:31]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4])[CH:17]=1)[CH3:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 86090154HCID 86090154, compound

Product 1

HCID 86602647HCID 86602647, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethyl phosphonoacetate (1.60 mL, 9.90 mmol) in 100 mL of THF was added sodium hydride (0.24 g of 60% dispersion in mineral oil, 9.90 mmol) portionwise. The mixture was stirred at ambient temperature for 30 min and then ethyl 4-ethyl-2-formyl-6-(trifluoromethyl)benzoate (1.81 g, 6.60 mmol) as a solution in THF. The reaction mixture was allowed to stir at ambient temperature for 30 min and then was diluted with water. The mixture was extracted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (elution with 15% EtOAc/hexane) to afford 2.1 g (96%) of the title compound as an off-white solid. 1H NMR (CDCl3): δ 7.72 (d, 1H, J=15.9 Hz), 7.62 (s, 1H), 7.53 (s, 1H), 6.44 (d, 1H, J=15.9 Hz), 4.45 (q, 2H, J=7.2 Hz), 3.81 (s, 3H), 2.75 (q, 2H, J=7.6 Hz), 1.40 (t, 3H, J=7.2 Hz), 1.28 (t, 3H, J=7.4 Hz).

Workup

  1. stirringto stir at ambient temperature for 30 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (elution with 15% EtOAc/hexane)

Sources & evidence

ORD record
ord-0600cfa3ed8b47aa8a8712eca275f288
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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