Triethyl phosphonoacetate → HCID 59585994, compound

HRID 1628769Notes

Reaction equation

HRID 1628769 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[C:30]2=[N:31][C:32]3[C:33](=[C:34]([CH:38]=O)[CH:35]=[CH:36][CH:37]=3)[N:29]2[CH2:28][CH2:27][CH2:26]1>O1CCCC1.O>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[C:30]2=[N:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34](/[CH:38]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:33]=3[N:29]2[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 57786099HCID 57786099, compound

Product 1

HCID 59585994HCID 59585994, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% in oil, 230 mg, 5.76 mmol) was added to a stirred solution of ethyl (diethoxyphosphoryl)acetate (1.94 g, 8.67 mmol) in tetrahydrofuran (14 mL) at 0° C. After stirring 10 min, 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (1.00 g, 2.88 mmol) in tetrahydrofuran (1.0 mL) was added to the mixture, and the mixture was stirred at room temperature for 12 hr. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with diisopropyl ether to give the title compound as a colorless powder (908 mg, 2.18 mmol, 76%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-a99b276e6a694c6289fae0b01dd97ea4
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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