Sodium hydride → HCID 66917857, compound

HRID 2235809Notes

Reaction equation

HRID 2235809 reaction equation
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)[CH3:2].[H-].[Na+].N1C2C(=CC=CC=2C=O)C=C1>C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734629Indole-7-carboxaldehydeHCID 21950087HCID 21950087, compound

Product 1

HCID 66917857HCID 66917857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(1H-Indol-7-yl)-acrylic acid ethyl ester (K-45). To a 100 mL round bottom flask which contained a suspension of NaH (60% in mineral oil, 320 mg, 8 mmol) in THF (20 mL) was added triethylphosphonoacetate (1.5 g, 6.6 mmol) at 0° C. The resulting mixture was allowed to warm to room temperature and stir at for 2 h and then cooled to 0° C. To this solution, 1H-indole-7-carboxaldehyde (K-44, 450 mg, 3 mmol) was added at 0° C. The resulting reaction mixture was allowed to warm to room temperature and stir for 2 h, then heated and stirred at 78° C. for 14 h. The reaction mixture was cooled to 5° C. and was quenched with the addition of saturated aqueous NH4Cl (15 mL) followed by extraction of EtOAc (3×30 mL). The combined organic extracts were washed with brine (2×20 mL), dried (Na2SO4), filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc/hexane=1:20-1:8) to afford desired 3-(1H-indol-7-yl)-acrylic acid ethyl ester K-45 (450 mg, 68%) as a white solid. MS(ESI−) m/z(216.3, 100%). 1HNMR, 13CNMR.

Workup

  1. customTo a 100 mL round bottom flask which contained
  2. temperaturecooled to 0° C
  3. customThe resulting reaction mixture
  4. temperatureto warm to room temperature
  5. stirringstir for 2 h
  6. temperatureheated
  7. stirringstirred at 78° C. for 14 h
  8. temperatureThe reaction mixture was cooled to 5° C.
  9. customwas quenched with the addition of saturated aqueous NH4Cl (15 mL)
  10. extractionfollowed by extraction of EtOAc (3×30 mL)
  11. washThe combined organic extracts were washed with brine (2×20 mL)
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. customthe solvent was removed under reduced pressure
  15. customThe residue was purified by flash chromatography (silica gel, EtOAc/hexane=1:20-1:8)

Sources & evidence

ORD record
ord-8c9ec071be154fa289a15a45a26b3be1
Source dataset
uspto-grants-2010_05
Patent number
US07714017B2

Reaction notes

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