Tetrafluoroboric acid → HCID 86651277, compound

HRID 1515044Notes

Reaction equation

HRID 1515044 reaction equation
N[C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[H+].[B-](F)(F)(F)F.N([O-])=O.[Na+].[CH2:22]([O:24][P:25]([CH:30]=[CH2:31])(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23]>O.CC([O-])=O.CC([O-])=O.[Pd+2].CO>[CH2:22]([O:24][P:25](/[CH:30]=[CH:31]/[C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23]

Participants

8

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 69629Diethyl vinylphosphonateHCID 123812354-Amino-2,6-dimethylbenzaldehydeHCID 23668193Sodium Nitrite

Product 1

HCID 86651277HCID 86651277, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-2,6-dimethylbenzaldehyde (149 mg, 1.0 mmol)) was taken up in enough 42% HBF4 until the suspension stirred well and then was cooled to 0° C. To this was added a solution of NaNO2 (69 mg, 1.0 mmol) in water (0.5 mL) slowly. After 30 minutes at 0° C., MeOH (3 mL) was added and followed by Pd(OAc)2 (7.5 mg) and vinylphosphonic acid diethyl ester (197 mg, 1.2 mmol). The reaction mixture was heated at 80° C. for 30 min and the suspension was filtered through Celite, washed with CH2Cl2, and the filtrate was extracted with CH2Cl2. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (4:1 then followed by 100% EtOAc) to give [(E)-2-(4-formyl-3,5-dimethylphenyl)-vinyl]-phosphonic acid diethyl ester as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 30 min
  2. filtrationthe suspension was filtered through Celite
  3. washwashed with CH2Cl2
  4. extractionthe filtrate was extracted with CH2Cl2
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-34f2fbabe198464291ff124aaba10a63
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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