4-Pyridinecarboxaldehyde → HCID 86654331, compound

HRID 1843601Notes

Reaction equation

HRID 1843601 reaction equation
COP([CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)(=O)OC.[H-].[Na+].[N:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1>C1COCC1>[N+:21]([C:17]1[CH:16]=[C:15]([C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:32][C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][CH:18]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 86654330HCID 86654330, compound

Product 1

HCID 86654331HCID 86654331, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[(3-Nitro-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-phosphonic acid dimethyl ester (40.7 g, 0.105 mol) was dissolved in dry THF (1 L) under nitrogen. Sodium hydride (60% suspension in mineral oil)(6.3 g, 0.158 mol, 1.5 eq) was added and the mixture was stirred for 10 minutes at room temperature. Neat 4-picolinaldehyde (10 mL, 0.105 mol, 1 eq) was then added dropwise and the mixture was heated to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure to ⅓ of the original volume and then diluted with water (500 mL). pH was adjusted to 7-8 by adding a saturated solution of NaHCO3 and the mixture was extracted with ethyl acetate (4×300 mL). The organic layer was dried over Na2SO4 and concentrated to dryness. An oil (37.7 g) was obtained, which was used without further purification in the following step.

Workup

  1. temperaturethe mixture was heated to 60° C.
  2. stirringstirred at this temperature for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with water (500 mL)
  5. additionby adding a saturated solution of NaHCO3
  6. extractionthe mixture was extracted with ethyl acetate (4×300 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ffc2601364a747e2863febc4178e0fb7
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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