Tetrahydrofuran → HCID 86591629, compound

HRID 495460Notes

Reaction equation

HRID 495460 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[N+:19]([C:22]1[C:29](OC)=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O)([O-:21])=[O:20].[NH4+].[Cl-].C1C[O:39][CH2:38]C1>O>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:9][CH:10]=[CH:24][C:23]1[CH:26]=[C:27]([O:39][CH3:38])[C:28]([O:32][CH3:33])=[CH:29][C:22]=1[N+:19]([O-:21])=[O:20])[CH3:3]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 86591629HCID 86591629, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of NaH (0.24 g, 6.0 mmol) in THF (30 mL) at 0° C. was added a solution of triethyl 4-phosphonocrotonate (1.0 g, 4.0 mmol) in THF (5 mL) dropwise. The solution was warmed to RT and stirred for 1 h. Nitroveratraldehyde (0.844 g, 4.0 mmol) was added to the mixture in one portion and the reaction was stirred for an additional 30 min at RT. NH4Cl (aq., sat., 3 mL) was added slowly to quench the reaction, followed by H2O (30 mL). The THF solvent was removed under reduced pressure and the resulting mixture was extracted with EtOAc (3×10 mL). The organic extracts were combined, washed with brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the mixture was purified by chromatography on silica gel to afford the title compound.

Workup

  1. stirringthe reaction was stirred for an additional 30 min at RT
  2. customto quench
  3. customthe reaction
  4. customThe THF solvent was removed under reduced pressure
  5. extractionthe resulting mixture was extracted with EtOAc (3×10 mL)
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e4c766c5234f499c9a39221c5686675d
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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