2,5-Dimethoxybenzaldehyde → HCID 71549888, compound

HRID 631940Notes

Reaction equation

HRID 631940 reaction equation
C(OP(=O)(OCC)O[CH2:6]/[CH:7]=[CH:8]/[C:9](=[O:16])[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)C.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:24]=1[CH:25]=O.CC(C)([O-])C.[K+]>C1COCC1>[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:24]=1/[CH:25]=[CH:6]/[CH:7]=[CH:8]/[C:9]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:16]

Participants

5

Reactant 3

HCID 667262,5-DimethoxybenzaldehydeHCID 23665647Potassium tert-butoxideHCID 117725439HCID 117725439, compound

Product 1

HCID 71549888HCID 71549888, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-diethyl 4-oxo-4-(piperidin-1-yl)but-2-enylphosphoric acid (50 mg, 0.17 mmol) and 2,5-dimethoxybenzaldehyde (28.4 mg, 0.17 mmol) were dissolved in THF (1.5 mL) at −10° C., and then potassium tert-butoxide (0.51 mL, 0.51 mmol) was added thereto, followed by stirring at the same temperature for 20 minutes under anhydrous reaction conditions. The temperature of the mixture was raised to room temperature, and the reaction was terminated by the addition of distilled water. After EtOAc was added, the oil layer was separated, followed by washing with distilled water and a saturated solution of NaCl, drying over anhydrous Na2SO4, and then filtering. The filtrate was distilled under reduced pressure, and the thus obtained residue was purified by column chromatography (hexane:EtOAc (2:1)) to give a target compound (40.7 mg, yield: 78.6%).

Workup

  1. customthe reaction was terminated by the addition of distilled water
  2. additionAfter EtOAc was added
  3. customthe oil layer was separated
  4. washby washing with distilled water
  5. dry with materiala saturated solution of NaCl, drying over anhydrous Na2SO4
  6. filtrationfiltering
  7. distillationThe filtrate was distilled under reduced pressure
  8. customthe thus obtained residue was purified by column chromatography (hexane:EtOAc (2:1))

Sources & evidence

ORD record
ord-a57d6999457148a184b8616f403bdc6c
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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